Abstract:
The present application described a new formulation for oxygen and/or water sensitive compounds with an inert material such as paraffin. The new formulation provides stability for the oxygen and/or water sensitive compounds in the air and can be handled easily. The new formulation of the present invention is useful as ligands and/or catalysts for preparation of pharmaceuticals, agrochemical, other fine chemicals and other synthetic compounds.

Description:
[0001]     This application is a continuation of U.S. provisional application 60/583,054 filed on Jun. 25, 2004. 
     
    
     FIELD OF THE INVENTION  
       [0002]     This invention relates to novel compositions of water and oxygen sensitive compounds and their method of preparation.  
       BACKGROUND OF THE INVENTION  
       [0003]     Many compounds, particularly substituted phosphine containing compounds and its related metal complexes are useful ligands and/or catalysts for production of pharmaceuticals, agrochemicals, and many other organic materials. These compounds can have decreased or lost the desired properties when handled in the air due to oxidation and/or hydrolysis in the presence of oxygen and moisture. Therefore, protection of these compounds from oxidation and/or hydrolysis is needed to ensure that the compounds can provide desired effects at the time of their ultimate use.  
         [0004]     For example, 1,3-(bis(mesityl)-2-imidazolidinylidene)dichloro-(phenylmethylene)(tricyclohexylphosphine)ruthenium is widely known for its applications in organic and polymer synthesis. Despite the obvious utility of this catalyst, its routine use is hindered by special storage requirements. Prolonged exposure to air and moisture deactivates the complex. Therefore, it is typically stored and handled under inert atmosphere, such as in the nitrogen filled glove box.  
         [0005]     In a similar instance, numerous chiral phosphine containing catalysts are useful homogeneous hydrogenation catalysts and have been used widely for preparation of pharmaceuticals, agrochemicals, flavors and other fine chemicals. Almost all these catalysts require protection from oxidation and/or hydrolysis to retain their desired activities.  
         [0006]     Numerous other compounds, such as those compounds listed in Aldrich and/or Strem chemical catalogs are sensitive to oxidation and/or hydrolysis.  
         [0007]     As the oxidative and hydrolytic damage of many compounds are obvious problems, the needs exist for effective and convenient means to prevent and/or slow the undesired oxidation and/or hydrolytic process. The needs also exist for convenient storage and handling of such compounds.  
       SUMMARY OF THE INVENTION  
       [0008]     This invention provides a stable composition for water and oxygen sensitive compounds comprising (a) at least one water and/or oxygen sensitive compound; and (b) at least one inert material with a melting point ranging from 20° C. to 250° C. The composition can contain from 0.1% to 99.9% of the water and/or oxygen sensitive compound and 99.9% to 0.1% of the inert material.  
         [0009]     This invention also provides a method of preparing a composition of the present invention. This method comprises dissolving or suspending a water and/or oxygen sensitive compounds in a inert material with a melting point ranging from 20° C. to 250° C.  
         [0010]     This invention also relates to the use a composition of the present invention in the preparation of pharmaceuticals, agrochemicals, flavors and other fine chemicals. 
     
    
     DETAILED DESCRIPTION OF THE INVENTION  
       [0011]     In the above recitations, the term “inert material” is a material, which is stable to its exposure to air and to the moisture in the air; and does not affect the desired activity of the water and/or oxygen sensitive compound. An embodiment of the inert material is paraffin, wax, fatty acids, or a polymer with a melting point ranging from 20° C. to 250° C.  
         [0012]     Preferred inert material is paraffin.  
         [0013]     Also preferred inert material is wax.  
         [0014]     The term “water and oxygen sensitive compounds” includes, but not limited to, organic and inorganic compounds, and a complex of the organic compound with metals. The metal in the complex of the organic compound includes, but not limited to, Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Y, Zr, Nb, Mo, Tc, Ru, Rh, Pd, Ag, Cd, In, Sn, Al, La, Hf, Ta, W, Re, Os, Ir, Pt, Au, Hg, and Eu.  
         [0015]     An embodiment of the water and oxygen sensitive compound is an organophosphine compund of Formula I;  
                         
 
 wherein 
        R 1 , R 2  and R 3  are each independently H; halogen; G; OG; NHG; NG 2 ; or C 1-32  alkyl, C 1-32  cycloalkyl; C 1-32  alkoxy, C 1-32  alkylamino, or C 1-32  dialkylamino each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO 2 , C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino, C 3 -C 6  cycloalkylamino, C 4 -C 7  (alkyl)cycloalkylamino, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminocarbonyl, and C 3 -C 8  dialkylaminocarbonyl; or     two of R 1 , R 2  and R 3  can be taken together to form a 5 to 8 membered ring optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO 2 , C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino, C 3 -C 6  cycloalkylamino, C 4 -C 7  (alkyl)cycloalkylamino, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminocarbonyl, and C 3 -C 8  dialkylaminocarbonyl; said 5 to 8 membered ring contains from 0-2 heteroatoms selected from the group consisting of N, O, and S; and said 5 to 8 membered ring is optionally fused with 1 or 2 optionally substituted phenyl or naphthyl ring;     G is a phenyl ring, naphthyl ring, 5- or 6-membered heteroaromatic rings, aromatic 8-, 9- or 10-membered fused carbobicyclic ring systems, or aromatic 8-, 9- or 10-membered fused heterobicyclic ring systems, each ring or ring system optionally substituted with one or more substituents selected from the group consisting of C 1 -C 4  alkyl, C 2 -C 4  alkenyl, C 2 -C 4  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 4  haloalkyl, C 2 -C 4  haloalkenyl, C 2 -C 4  haloalkynyl, C 3 -C 6  halocycloalkyl, halogen, CN, NO 2 , C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino, C 3 -C 6  cycloalkylamino, C 4 -C 7  (alkyl)cycloalkylamino, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminocarbonyl, and C 3 -C 8  dialkylaminocarbonyl;        
 
         [0019]     A further embodiment of the water and oxygen sensitive compound is an organophosphine compound of Formula II;  
                         
 
 wherein 
        R 4  and R 5  are each independently phenyl, phenoxy, C 1-10  alkyl, C 1-10  cycloalkyl; C 10  alkoxy, C 1-10  alkylamino, or C 1-10  dialkylamino each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO 2 , C 1-8  alkyl, C 1-8  alkoxy, C 1-8  alkylamino, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino, C 3 -C 6  cycloalkylamino, C 4 -C 7  (alkyl)cycloalkylamino, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminocarbonyl, and C 3 -C 8  dialkylaminocarbonyl; or     each R 4  and R 5  can be taken together to form a 4 to 8 membered ring optionally substituted with one or more substituents selected from the group consisting of halogen, OH, CN, NO 2 , benzyl, C 1-8  alkyl, C 1-8  alkoxy, C 1-8  alkylamino, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino, C 3 -C 6  cycloalkylamino, C 4 -C 7  (alkyl)cycloalkylamino, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminocarbonyl, and C 3 -C 8  dialkylaminocarbonyl; said 5-8 membered saturated, partially saturated or unsaturated ring contains from 0-2 heteroatoms selected from the group consisting of N, O, and S; and said 5-8 membered saturated, partially saturated or unsaturated ring is optionally fused with 1 or 2 optionally substituted phenyl or naphthyl ring; and     L is a 2 to 8 atom bridge containing C and/or O.        
 
         [0023]     In the above recitations, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio and butylthio isomers. “Alkylsulfinyl” includes both enantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl” include CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl isomers. Examples of “alkylsulfonyl” include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 , CH 3 CH 2 CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2  and the different butylsulfonyl isomers. “Cyanoalkyl” denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH 2 , NCCH 2 CH 2  and CH 3 CH(CN)CH 2 . “Alkylamino”, “dialkylamino”, and the like, are defined analogously to the above examples. “Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term “cycloalkylamino” includes the same groups linked through a nitrogen atom such as cyclopentylamino and cyclohexylamino.  
         [0024]     The term “hetero” in connection with rings or ring systems refers to a ring or ring system in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. The terms “heteroaromatic ring or ring system” and “aromatic fused heterobicyclic ring system” includes fully aromatic heterocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the Hückel rule is satisfied). The heterocyclic ring or ring system can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.  
         [0025]     The term “halogen”, either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl” or “halocycloalkyl”, said alkyl or cycloalkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F 3 C, ClCH 2 , CF 3 CH 2  and CF 3 CCl 2 . The terms “haloalkenyl”, “haloalkynyl”, “haloalkoxy”, “haloalkylthio”, and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkenyl” include (Cl) 2 C═CHCH 2  and CF 3 CH 2 CH═CHCH 2 . Examples of “haloalkynyl” include HC≡CCHCl, CF 3 C≡C, CCl 3 C≡C and FCH 2 C≡CCH 2 . Examples of “haloalkoxy” include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O. Examples of “haloalkylthio” include CCl 3 S, CF 3 S, CCl 3 CH 2 S and ClCH 2 CH 2 CH 2 S. Examples of “haloalkylsulfinyl” include CF 3 S(O), CCl 3 S(O), CF 3 CH 2 S(O) and CF 3 CF 2 S(O). Examples of “haloalkylsulfonyl” include CF 3 S(O) 2 , CCl 3 S(O) 2 , CF 3 CH 2 S(O) 2  and CF 3 CF 2 S(O) 2 .  
         [0026]     Examples of “alkylcarbonyl” include C(O)CH 3 , C(O)CH 2 CH 2 CH 3  and C(O)CH(CH 3 ) 2 . Examples of “alkoxycarbonyl” include CH 3 C(═O), CH 3 CH 2 C(═O), CH 3 CH 2 CH 2 C(═O), (CH 3 ) 2 CHOC(═O) and the different butoxy- or pentoxycarbonyl isomers. Examples of “alkylaminocarbonyl” include CH 3 NHC(═O), CH 3 CH 2 NHC(═O), CH 3 CH 2 CH 2 NHC(═O), (CH 3 ) 2 CHNHC(═O) and the different butylamino- or pentylaminocarbonyl isomers. Examples of “dialkylaminocarbonyl” include (CH 3 ) 2 NC(═O), (CH 3 CH 2 ) 2 NC(═O), CH 3 CH 2 (CH 3 )NC(═O), CH 3 CH 2 CH 2 (CH 3 )NC(═O) and (CH 3 ) 2 CHN(CH3)C(═O).  
         [0027]     The total number of carbon atoms in a substituent group is indicated by the “C i -C j ” prefix where i and j are numbers from 1 to 32. For example, C 1 -C 3  alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C 2  alkoxyalkyl designates CH 3 OCH 2 ; C 3  alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2  or CH 3 CH 2 OCH 2 ; and C 4  alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2  and CH 3 CH 2 OCH 2 CH 2 .  
         [0028]     The composition of the present invention can be prepared by adding the oxygen and/or water sensitive compounds to the molten inert material to give a homogeneous or heterogeneous mixture. For example, the oxygen and/or water sensitive compound can be added to the molten paraffin or wax to give a homogeneous or heterogeneous mixture. The homogeneous or heterogeneous mixture can be solidified upon cooling and can be cut into useful pieces and stored without precautionary protection from oxygen or water. The mixture can subsequently handled and weighted in the air.  
         [0029]     The composition of the present invention can also be prepared by adding the molten inert material to the oxygen and/or water sensitive compound to give a homogeneous or heterogeneous mixture. For example, molten paraffin can be added to the oxygen and/or water sensitive compound to give a homogeneous or heterogeneous mixture. The homogeneous or heterogeneous mixture can be solidified upon cooling and can be cut into useful pieces for its use.  
         [0030]     The composition of the present invention can also be prepared by heating a pre-mixture of the oxygen and/or water sensitive compound and the inert material. For example, paraffin and an oxygen and/or water sensitive compound can be mixed and subsequently heated to give a homogeneous or heterogeneous mixture. The homogeneous or heterogeneous mixture can be solidified upon cooling and can be cut into useful pieces for its use.  
         [0031]     The composition of the present invention can also be prepared by mixing the oxygen and/or water sensitive compound and the inert material in a suitable organic solvent. For example, the paraffin and the oxygen and/or water sensitive compound solution in a suitable organic solvent can be mixed to give a homogeneous or heterogeneous solution. The homogeneous or heterogeneous solution can be solidified upon removing the organic solvent.  
         [0032]     For example, the Grubbs catalyst, 1,3-(bis(mesityl)-2-imidazolidinylidene)-dichloro-(phenylmethylene)(tricyclohexylphosphine)ruthenium, can be weighed in a nitrogen atmosphere drybox and dispersed (11 wt %) in molten paraffin wax to give a homogeneous purple liquid. This mixture can be allowed to cool before removal from the drybox. The ruthenium complex-paraffin mixture can then be cut into useful pieces and stored without protection from laboratory air. This makes it convenient to weigh out small quantities of the otherwise easily dispersed ruthenium complex. The mixture can then be stored under normal laboratory conditions for many months without concern over the loss of catalytic activity. A sample prepared as described here can be stored for at least 22 months with no special storage precautions without loss of most of the catalyst&#39;s activity. For detailed reaction illustration of such prepared catalyst, see  J. Org. Chem.  2003, 68, 6047-6048  
       EXAMPLE  
     Preparation of 1,3-(bis(mesityl)-2-imidazolidinylidene)-dichloro-(phenylmethylene)(tricyclohexylphosphine)ruthenium in paraffin  
       [0033]     In a nitrogen atmosphere drybox, 1,3-(bis(mesityl)-2-imidazolidinylidene)-dichloro-(phenylmethylene)(tricyclohexylphosphine)ruthenium (Grubbs&#39; catalyst 1) (1.27 g, 1.50 mmol) was combined in a 25 mL beaker with paraffin wax (paraffin wax for canning, mp=48-50° C., 8.73 g). The mixture was warmed to melting in a heating mantle and stirred with a glass rod to apparent homogeneity (one min). After cooling, the solid was removed from the drybox, broken into useful-sized pieces, and stored in a brown glass bottle without further protection.  
         [0034]     In an embodiment of the present invention, the water and oxygen sensitive compounds include, but not limited to compounds in Table 1.  
                   TABLE 1                       CAS Number   Chemical name                   169689-05-8   N,N′-(1S,2S)-1,2-cyclohexanediylbis[2-(diphenylphosphino) benzamide;       76740-45-9   (1R,2R,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-diylbis[diphenyl-, rel           phosphine       69227-47-0   tris(3,5-dimethylphenyl) phosphine       63589-61-7   1,2-ethanediylbis[(2-methoxyphenyl)phenyl phosphine       55102-19-7   chlorohydrotris(triphenylphosphine)-, (TB-5-13) ruthenium       53204-14-1   di-μ-chlorobis[1,2-ethanediylbis[diphenylphosphine-κP]]di rhodium       15909-92-9   3,3′-(phenylphosphinidene)bis propanenitrile       12150-46-8   1,1′-bis(diphenylphosphino) ferrocene       7688-25-7   1,4-butanediylbis[diphenyl] phosphine       6163-58-2   tris(2-methylphenyl) phosphine       5518-52-5   tri-2-furanyl phosphine       2622-14-2   tricyclohexyl phosphine       1314-80-3   Phosphorus sulfide (P2S5)       998-40-3   tributyl phosphine       443347-10-2   4,4′-bis[bis(3,5-dimethylphenyl)phosphino]-2,2′,6,6′-tetramethoxy-, (3S)           3,3′-bipyridine       406680-94-2   1-(diphenylphosphino)-2-[(1R)-1-           [(diphenylphosphino)methylamino]ethyl]-, (1R) ferrocene       305818-67-1   [(1,2,5,6-η)-1,5-cyclooctadiene][(2R,2′R,5R,5′R)-1,1′-(1,2-           ethanediyl)bis[2,5-dimethylphospholane-κP]]-,, tetrafluoroborate(1−)           rhodium(1+)       290347-66-9   1,1′-bis[(2S,4S)-2,4-diethyl-1-phosphetanyl]-, ferrocene       255884-98-1   1-[(R)-(dimethylamino)[2-(diphenylphosphino)phenyl]methyl]-2-           (diphenylphosphino)-, (2R) ferrocene       221012-82-4   4,4′-bis(diphenylphosphino)-2,2′,6,6′-tetramethoxy-, (3R) 3,3′-bipyridine       213343-69-2   Rhodium(1+), [(1,2,5,6-η)-1,5-cyclooctadiene][(2S,2′S,5S,5′S)-1,1′-(1,2-           ethanediyl)bis[2,5-dimethylphospholane-κP]]-, salt with           trifluoromethanesulfonic acid (1:1)       213343-65-8   [(1,2,5,6-η)-1,5-cyclooctadiene][(2S,2′S,5S,5′S)-1,1′-(1,2-           ethanediyl)bis[2,5-dimethylphospholane-κP]] rhodium(1+),           tetrafluoroborate(1−)       213343-64-7   [(1,2,5,6-η)-1,5-cyclooctadiene][(2S,2′S,5S,5′S)-1,1′-(1,2-           phenylene)bis[2,5-diethylphospholane-κP]] rhodium(1+),           tetrafluoroborate(1−)       212210-87-2   [(1R)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-           κP]]dichloro[(1S,2S)-1,2-diphenyl-1,2-ethanediamine-κN,κN′]-, (OC-6-           13) ruthenium       212143-24-3   Ruthenium, [(1S)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-           κP]][(2S)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine-           κN,κN′]dichloro-, (OC-6-14)-       212143-23-2   Ruthenium, [(1R)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-           κP]]dichloro[(1R,2R)-1,2-diphenyl-1,2-ethanediamine-κN,κN′]-, (OC-6-           13)-       210057-23-1   [(1,2,5,6-η)-1,5-cyclooctadiene][(2R,2′R,5R,5′R)-1,1′-(1,2-           phenylene)bis[2,5-dimethylphospholane-κP]] rhodium(1+),           tetrafluoroborate(1−)       208248-67-3   N,N′-[(1R)-5,5′,6,6′,7,7′,8,8′-octahydro[1,1′-binaphthalene]-2,2′-           diyl]bis[P,P-diphenyl] phosphinous amide       205064-10-4   [(1,2,5,6-η)-1,5-cyclooctadiene][(2S,2′S,5S,5′S)-1,1′-(1,2-           phenylene)bis[2,5-dimethylphospholane-κP]] rhodium(1+),           tetrafluoroborate(1−)       203000-59-3   [(2,3,5,6-η)-bicyclo[2.2.1]hepta-2,5-diene][(1R,1′R)-1,2-           ethanediylbis[(1,1-dimethylethyl)methylphosphine-κP]] rhodium(1+),           tetrafluoroborate(1−)       194149-25-2   P,P-bis(3,5-dimethylphenyl)-N,N-diethyl phosphinous amide       192463-40-4   tricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene-5,11-           diylbis[diphenyl] phosphine,       187682-63-9   [(1,2,5,6-η)-1,5-cyclooctadiene][(2R,2′R,5R,5′R)-1,1′-(1,2-           phenylene)bis[2,5-dimethylphospholane-κP]] rhodium(1+), salt with           trifluoromethanesulfonic acid (1:1)       185449-80-3   N,N-dimethyl-, (11bS)-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-           amine,       184095-69-0   1-[(1R)-1-[bis(3,5-dimethylphenyl)phosphino]ethyl]-2-           (diphenylphosphino)-, (2R)- Ferrocene       177750-25-3   [(1,2,5,6-η)-1,5-cyclooctadiene][1,1′-(1,2-ethanediyl)bis[2,5-           dimethylphospholane]-P,P′]-, [2R-[1(2′R*,5′R*),2α,5β]] Rhodium(1+),           salt with trifluoromethanesulfonic acid (1:1)       167416-28-6   1-(dicyclohexylphosphino)-2-[(1R)-1-(dicyclohexylphosphino)ethyl]-,           (R)- Ferrocene       166172-69-6   bis[3,5-bis(trifluoromethyl)phenyl] phosphine       158214-06-3   α-D-Glucopyranoside, methyl, 2,6-dibenzoate 3,4-bis[bis(3,5-           dimethylphenyl)phosphinite]       155830-69-6   1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-           (diphenylphosphino)-, (1R)- Ferrocene       155806-35-2   1-[(1R)-1-(dicyclohexylphosphino)ethyl]-2-(diphenylphosphino)-, (R)-           Ferrocene       155613-52-8   4-chloro-, (11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin,       148461-14-7   2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-4-(1-methylethyl)-, (4S)-           Oxazole       147253-67-6   1,1′-(1,2-phenylene)bis[2,5-dimethyl-, [2R-[1(2′R*,5′R*),2α,5β]]           Phospholane       145926-28-9   [(1R)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-           κP]]chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]           ruthenium(1+), chloride       145416-77-9   [1,1′-binaphthalene]-2,2′-diylbis[bis(3,5-dimethylphenyl) phosphine       142691-70-1   1,1′-bis(dichlorophosphino) ferrocene       142184-30-3   [(1,2,5,6-η)-1,5-cyclooctadiene][(2S,2′S,5S,5′S)-1,1′-(1,2-           phenylene)bis[2,5-diethylphospholane-κP]] rhodium(1+), salt with           trifluoromethanesulfonic acid (1:1)       139139-93-8   [(1S)-5,5′,6,6′,7,7′,8,8′-octahydro[1,1′-binaphthalene]-2,2′-           diyl]bis[diphenyl] phosphine       139139-92-7   (1R)-[1,1′-binaphthalene]-2,2′-diylbis[dicyclohexyl]phosphine       139139-86-9   [(1R)-5,5′,6,6′,7,7′,8,8′-octahydro[1,1′-binaphthalene]-2,2′-           diyl]bis[diphenyl]phosphine       137219-86-4   (1R)-[1,1′-binaphthalene]-2,2′-diylbis[bis(3,5-dimethylphenyl) phosphine       137156-22-0   Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin, 4-chloro-, (11bS)-       136802-85-2   bis(4-methoxy-3,5-dimethylphenyl) phosphinous chloride       136779-28-7   1,1′-(1,2-phenylene)bis[2,5-diethyl-, (2S,2′S,5S,5′S)- Phospholane       136779-27-6   1,1′-(1,2-ethanediyl)bis[2,5-diethyl-, (2S,2′S,5S,5′S)- Phospholane       136779-26-5   1,1′-(1,2-ethanediyl)bis[2,5-dimethyl-, (2S,2′S,5S,5′S)- Phospholane       136739-32-7   [(1R)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-κP]]bis[(1,2,3-           η)-2-methyl-2-propenyl] ruthenium       136735-95-0   1,1′-(1,2-phenylene)bis[2,5-dimethyl-, (2S,2′S,5S,5′S)- Phospholane       136705-77-6   [(1,2,5,6-η)-1,5-cyclooctadiene][(2R,2′R,5R,5′R)-1,1′-(1,2-           phenylene)bis[2,5-diethylphospholane-KP]] rhodium(1+), salt with           trifluoromethanesulfonic acid (1:1)       136705-75-4   [(1,2,5,6-η)-1,5-cyclooctadiene][(2S,2′S,5S,5′S)-1,1′-(1,2-           phenylene)bis[2,5-dimethylphospholane-κP]] rhodium(1+), salt with           trifluoromethanesulfonic acid (1:1)       136705-65-2   1,1′-(1,2-phenylene)bis[2,5-bis(1-methylethyl)-, (2R,2′R,5R,5′R)-           Phospholane       136705-64-1   1,1′-(1,2-phenylene)bis[2,5-diethyl-, (2R,2′R,5R,5′R)- Phospholane       136705-62-9   1,1′-(1,2-ethanediyl)bis[2,5-diethyl-, (2R,2′R,5R,5′R)- Phospholane       135139-00-3   [(1S)-[1,1′-binaphthalene]-2,2′-diyl]bis[bis(3,5-dimethylphenyl)]           phosphine       134524-84-8   Ruthenium, [[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-           κP]]dichloro-, [SP-4-2-(S)]-       133773-19-0   Ruthenium, [[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine]-           P,P′]bis[(1,2,3-η)-2-methyl-2-propenyl]-, (S)-       133545-17-2   [(1S)-6,6′-dimethoxy[1,1′-biphenyl]-2,2′-diyl]bis[diphenyl] phosphine       133545-16-1   [(1R)-6,6′-dimethoxy[1,1′-biphenyl]-2,2′-diyl]bis[diphenyl] phosphine       132071-87-5   Ruthenium, [(1R)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-           κP]]dichloro-, (SP-4-2)-       130004-33-0   [(1S)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-           κP]]chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]           ruthenium(1+), chloride       129648-07-3   1,1′-(1,2-ethanediyl)bis[2,5-dimethyl-, (2R,2′R,5R,5′R)- Phospholane       127797-02-8   [[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[bis(4-           methoxy-3,5-dimethylphenyl) phosphine       122977-44-0   [[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[bis(4-           methoxy-3,5-dimethylphenyl) phosphine       122708-97-8   bis(4-methoxy-3,5-dimethylphenyl) phosphine       121457-42-9   (1S)-[1,1′-binaphthalene]-2,2′-diylbis[dicyclohexyl] phosphine           ethanediyl]bis[diphenylphosphine-κP]]rhodium(1+), perchlorate       64896-28-2   [(1S,2S)-1,2-dimethyl-1,2-ethanediyl]bis[diphenyl] phosphine       62793-31-1   bis[(1,2,5,6-η)-1,5-cyclooctadiene] rhodium(1+), hexafluorophosphate(1−)       62336-24-7   (2-bromophenyl)diphenyl phosphine       61478-29-3   Pyrrolidine, 4-(diphenylphosphino)-2-[(diphenylphosphino)methyl]-,           (2S,4S)-       61478-28-2   1-Pyrrolidinecarboxylic acid, 4-(diphenylphosphino)-2-           [(diphenylphosphino)methyl]-, 1,1-dimethylethyl ester, (2S,4S)-       56977-92-5   [(1,2,5,6-η)-1,5-cyclooctadiene][(1R, 1′R)-1,2-ethanediylbis[(2-           methoxyphenyl)phenylphosphine-κP]] rhodium(1+), tetrafluoroborate(1−)       56183-63-2   tetrakis(1-methylethyl) phosphorodiamidous chloride       55739-58-7   1,2-ethanediylbis[(2-methoxyphenyl)phenyl-, [R-(R*,R*)]- Phosphine       55700-44-2   1-[(1R)-1-(dimethylamino)ethyl]-2-(diphenylphosphino)-, (2R)-           Ferrocene       55650-59-4   1-[(1S)-1-(dimethylamino)ethyl]-1′,2-bis(diphenylphosphino)-, (2S)-           Ferrocene       55650-58-3   1-[(1S)-1-(dimethylamino)ethyl]-2-(diphenylphosphino)-, (2R)-           Ferrocene       53111-20-9   (2-methoxyphenyl)diphenyl] phosphine       50763-75-2   [[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-           diyl]bis(methylene)]bis[diphenyl Phosphine,       40244-90-4   bis(1-methylethyl) phosphinous chloride       37002-48-5   [[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-           diyl]bis(methylene)]bis[diphenyl] phosphine       36042-94-1   bis(2-methylphenyl) phosphinous chloride       32993-05-8   chloro(η5-2,4-cyclopentadien-1-yl)bis(triphenylphosphine) ruthenium       32305-98-9   [[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-           diyl]bis(methylene)]bis[diphenyl] phosphine       28240-69-9   1,2-ethanediylbis phosphonous dichloride       25979-07-1   (1,1-dimethylethyl) phosphonous dichloride       25235-15-8   (1-methylethyl) phosphonous dichloride       18437-78-0   tris(4-fluorophenyl) phosphine       16941-11-0   hexafluoro phosphate(1−), ammonium       16523-54-9   dicyclohexyl phosphinous chloride       15873-72-0   dicyclohexyl phosphinic chloride       15529-49-4   dichlorotris(triphenylphosphine) ruthenium       15475-27-1   diphenyl phosphine, potassium salt       14973-89-8   Rhodium, bromotris(triphenylphosphine)-, (SP-4-2)-       14694-95-2   Rhodium, chlorotris(triphenylphosphine)-, (SP-4-2)-       14647-23-5   Nickel, dichloro[1,2-ethanediylbis[diphenylphosphine-κP]]-, (SP-4-2)-       14221-02-4   Platinum, tetrakis(triphenylphosphine)-, (T-4)-       14221-01-3   Palladium, tetrakis(triphenylphosphine)-, (T-4)-       13965-03-2   dichlorobis(triphenylphosphine) palladium       13685-23-9   bis(3-methylphenyl) phosphinous chloride       10150-27-3   2-[2-(diphenylphosphino)ethyl] pyridine       10025-87-3   Phosphoric trichloride       7719-12-2   Phosphorous trichioride       6737-42-4   1,3-propanediylbis[diphenyl] phosphine       5518-62-7   1,2-ethanediylbis phosphine       4848-43-5   2-(diphenylphosphino) ethanamine       4541-02-0   diphenyl phosphine, lithium salt       3487-44-3   methylenetripheny phosphorane       3348-44-5   tetramethyl phosphorodiamidous chloride       2844-89-5   cyclohexyl phosphonous dichloride       1663-45-2   1,2-ethanediylbis[diphenyl] phosphine       1636-14-2   N,N,N′,N′-tetraethyl-P-phenyl phosphonous diamide       1608-26-0   hexamethyl phosphorous triamide       1498-40-4   ethyl phosphonous dichloride       1079-66-9   diphenyl phosphinous chloride       1069-08-5   diethyl phosphoramidous dichloride       1038-95-5   tris(4-methylphenyl) phosphine       855-38-9   tris(4-methoxyphenyl) phosphine       829-85-6   diphenyl phosphine       829-84-5   dicyclohexyl phosphine       819-19-2   bis(1,1-dimethylethyl) phosphine       811-62-1   dimethyl phosphinous chloride       686-69-1   diethyl phosphinous chloride       685-83-6   tetraethyl phosphorodiamidous chloride       676-83-5   methyl phosphonous dichloride       644-97-3   phenyl phosphonous dichloride       638-21-1   phenyl phosphine       603-35-0   triphenyl phosphine       589-57-1   Phosphorochloridous acid, diethyl ester       121-45-9   Phosphorous acid, trimethyl ester       1305-99-3   Calcium phosphide;       12261-30-2   Cyclopentadienyl(triethylphosphine)copper (I);       135707-05-0   Trimethylphosphine(hexafluoroacetylacetonato)copper (I);       12063-98-8   Gallium phosphide (99.999%-Ga) PURATREM;       15529-90-5   Chlorotriethylphosphine gold (I);       15278-97-4   Chlorotrimethylphosphine gold (I);       14243-64-2   Chlorotriphenylphosphine gold (I);       22398-80-7   Indium phosphide (99.999%-In) PURATREM;       14871-41-1   Chlorocarbonylbis(triphenylphosphine)iridium (I); VASKA&#39;S           COMPLEX       583844-38-6   ((4S,5S)-(−)-O-[1-Benzyl-1-(5-methyl-2-phenyl-4,5-dihydro-oxazol-4-yl)-           2-phenylethyl]-dicyclohexylphosphinite)(1,5-COD)iridium (I) tetrakis-           (3,5-bis(trifluoromethyl)phenyl)borate;       17250-25-8   Hydridocarbonyltris(triphenylphosphine)iridium (I);       405235-55-4   ((4S,5S)-(+)-O-[1-Benzyl-1-(5-methyl-2-phenyl-4,5-dihydro-oxazol-4-           yl)-2-phenylethyl]-diphenylphosphinite)(1,5-COD)iridium (I) tetrakis-           (3,5-bis(trifluoromethyl)phenylborate;       64536-78-3   (Tricyclohexylphosphine)(1,5-cyclooctadiene)(pyridine)iridium           (I)hexafluorophosphate; CRABTREE&#39;S CATALYST       84680-95-5   1,1′-Bis(di-t-butylphosphino)ferrocene;       494227-35-9   (S,S)-(+)-2,2′-Bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1′-           bis(dicyclohexylphosphino)ferrocene;       494227-37-1   (S,S)-(−)-2,2′-Bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1′-           di[bis(3,5-dimethyl-4-methoxyphenyl)phosphino]ferrocene;       210842-74-3   (S,S)-(−)-2,2′-Bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1′-           bis(diphenylphosphino)ferrocene;       494227-36-0   (S,S)-(−)-2,2′-Bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1′-           di[bis(3,5-trifluoromethylphenyl)phosphino]ferrocene;       360048-63-1   (R)-(−)-1-[(S)-2-(Bis(3,5-dimethyl-4-           methoxyphenyl)phosphino)ferrocenyl]ethyldicyclohexylphosphine;           (R)-(+)-1,1′-Bis(diphenylphosphino)-2,2′-bis(N,N-di-i-           propylamido)ferrocene (R)-CTH-JAFAPhos;       97239-80-0   1,1′-Bis(di-i-propylphosphino)ferrocene;       246231-79-8   (R)-(−)-1-[(S)-2-(Bis(4-           trifluoromethylphenyl)phosphino)ferrocenyl]ethyl-di-t-butylphosphine;       292638-88-1   (R)-(−)-1-[(S)-2-(Di(3,5-bis-           trifluoromethlphenyl)phosphino)ferrocenyl]ethyldicyclohexylphosphine       166172-63-0   (R)-(−)-1-[(S)-2-(Di(3,5-bis-           trifluoromethylphenyl)phosphino)ferrocenyl]ethyldi(3,5-           dimethylphenyl)phosphine;       494227-38-2   (S)-(+)-[(R)-2-Dicyclohexylphosphinoferrocenyl](N,N-           dimethylamino)(2-dicyclohexylphosphinophenyl)methane;       158923-11-6   (R)-(−)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-           butylphosphine;       158923-07-0   (S)-(+)-1-[(R)-2-           (Dicyclohexylphosphino)ferrocenyl]ethyldicyclohexylphosphine;       158923-09-2   (R)-(−)-1-[(S)-2-           (Dicyclohexylphosphino)ferrocenyl]ethyldiphenylphosphine;       162291-01-2   (S)-(+)-1-[(R)-2-           (Dicyclohexylphosphino)ferrocenyl]ethyldiphenylphosphine;       494227-32-6   (R)-(+)-1-[(R)-2-(2′-           Dicyclohexylphosphinophenyl)ferrocenyl]ethyldi(bis-3,5-           trifluoromethylphenyl)phosphine;       494227-30-4   (R)-(+)-1-[(R)-2-(2′-Di(3,5-dimethyl-4-           methoxyphenyl)phosphinophenyl)ferrocenyl]ethyldi(bis-3,5-           trifluoromethylphenyl)pho;           (S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldi-t-           butylphosphine;       360048-66-4   (R)-(+)-1-[(R)-2-           (Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine; (R)-(R)-           JOSIPHOS       162291-02-3   (S)-(+)-1-[(R)-2-           (Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine ethanol           adduct; (S)-(R)-JOSIPHOS       387868-06-6   (R)-(−)-1-[(R)-2-(2′-Diphenylphosphinophenyl)ferrocenyl]ethyldi(bis-3,5-           trifluoromethylphenyl)phosphine;       388079-60-5   (R)-(−)-1-[(R)-2-(2′-           Diphenylphosphinophenyl)ferrocenyl]ethyldicyclohexylphosphine;       494227-31-5   (R)-(+)-1-[(R)-2-(2′-Diphenylphosphinophenyl)ferrocenyl]ethyldi(3,5-           xylyl)phosphine;       494227-33-7   (R)-(+)-1-[(R)-2-(2′-Di(3,5-           xylyl)phosphinophenyl)ferrocenyl]ethyldi(3,5-xylyl)phosphine;       312959-24-3   1,2,3,4,5-Pentaphenyl-1′-(di-t-butylphosphino)ferrocene; CTC-Q-PHOS       15629-92-2   1,3-Bis(diphenylphosphino)propane nickel (II) chloride;       14126-37-5   Bis(triphenylphosphine)nickel (II) bromide;       14264-16-5   Bis(triphenylphosphine)nickel (II) chloride;       13007-90-4   Bis(triphenylphosphine)nickel dicarbonyl;       67292-34-6   Dichloro[1,1′-bis(diphenylphosphino)ferrocene]nickel (II);       13859-65-9   Tetrakis(trifluorophosphine)nickel (0);       31277-98-2   Bis[1,2-bis(diphenylphosphino)ethane]palladium (0);       53199-31-8   Bis(tri-t-butylphosphine)palladium (0);       33309-88-5   Bis(tricyclohexylphosphine)palladium (0);       359803-53-5   Chloro(di-2-norbornylphosphino)(2′-dimethylamino-1,1′-biphenyl-2-           yl)palladium (II);       614753-51-4   Chloro(di-2-norbornylphosphino)(2-dimethylaminomethylferrocen-1-           yl)palladium (II);       172418-32-5   trans-Di(mu-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium (II);       14588-08-0   Diacetatobis(triphenylphosphine)palladium (II);       185812-86-6   Di--bromobis(tri-t-butylphosphino)dipalladium (I);       19978-61-1   Dichloro(1,2-bis(diphenylphosphino)ethane)palladium (II);       72287-26-4   Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II)           dichloromethane adduct;       29934-17-6   trans-Dichlorobis(tricyclohexylphosphine)palladium (II);       40691-33-6   trans-Dichlorobis(tri-o-tolylphosphine)palladium (II);           Buchwald Biaryl Phosphine Ligand Kit for Aromatic Carbon-Heteroatom           Bond Formation and Suzuki Coupling;           Phosphine Ligand Kit for Palladium-Catalyzed Carbon-Carbon and           Carbon-Heteroatom Bond Formation;           Acetato(2′-di-t-butylphosphino-1,1′-biphenyl-2-yl)palladium (II);       395116-70-8   Benzyldi-1-adamantylphosphine; [cataCXium ® ABn];       7650-91-1   Benzyldiphenylphosphine;       121954-50-5   alpha,alpha′-Bis(di-t-butylphosphino)-o-xylene;       37170-64-2   1,2-Bis(dichlorophosphino)-1,2-dimethylhydrazine;       28240-68-8   Bis(dichlorophosphino)methane;       23743-26-2   1,2-Bis(dicyclohexylphosphino)ethane;       137349-65-6   Bis(dicyclohexylphosphino)methane;       6411-21-8   1,2-Bis(diethylphosphino)ethane;       23936-60-9   1,2-Bis(dimethylphosphino)ethane;       64065-08-3   Bis(dimethylphosphino)methane;       76858-94-1   1,2-Bis(dipentafluorophenylphosphino)ethane;       5112-95-8   Bis(diphenylphosphino)acetylene;       2960-37-4   N,N-Bis(diphenylphosphino)amine;       229177-79-1   (S)-(−)-2,2′-Bis(N-diphenylphosphinoamino)-5,5′,6,6′,7,7′,8,8′-octahydro-           1,1′-binaphthyl; CTH-(S)-BINAM;       13991-08-7   1,2-Bis(diphenylphosphino)benzene;       84783-64-2   2,2′-Bis(diphenylphosphino)-1,1′-biphenyl; BIPHEP;       398127-98-5   R-6,6′-Bis(diphenylphosphino)-1,1′-biphenyl-2,2′-diylbis(acetate); (R)-           Methyl Soniphos;           S-6,6′-Bis(diphenylphosphino)-1,1′-biphenyl-2,2′-diylbis(acetate); (S)-           Methyl Soniphos;       398128-03-5   R-6,6′-Bis(diphenylphosphino)-1,1′-biphenyl-2,2′-           diylbis(cyclohexylcarboxylate); (R)-Cyclohexyl Soniphos;           S-6,6′-Bis(diphenylphosphino)-1,1′-biphenyl-2,2′-           diylbis(cyclohexylcarboxylate); (S)-Cyclohexyl Soniphos;       301847-89-2   R-(−)-1,13-Bis(diphenylphosphino)-7,8-dihydro-6H-           dibenzo[f,h][1,5]dioxonin; (R)-C3-TUNEPHOS;       984-43-0   1,2-Bis(diphenylphosphino)ethane monooxide;       983-80-2   cis-1,2-Bis(diphenylphosphino)ethylene;       23582-02-7   Bis(2-diphenylphosphinoethyl)phenylphosphine; TRIPHOS;       2071-20-7   Bis(diphenylphosphino)methane;       23176-18-3   Bis(diphenylphosphino)methane monooxide;           (R)-(−)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane; (R)-           PHANEPHOS;       261733-18-0   4,6-Bis(diphenylphosphino)phenoxazine; NIXANTPHOS;       166330-10-5   Bis(2-diphenylphosphinophenyl)ether; DPEphos;       85685-99-0   1,3-Bis(diphenylphosphino)propane monooxide;       503538-69-0   R-(−)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-           benzodioxole, dichloromethane adduct; (R)-DIFLUORPHOS TM;       503538-70-3   S-(+)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-           benzodioxole, dichloromethane adduct; (S)-DIFLUORPHOS TM;           R-(+)-6,6′-Bis(diphenylphosphino)-2,2′,3,3′-tetrahydro-5,5′-bi-1,4-           benzodioxin; (R)-SYNPHOS TM;           S-(−)-6,6′-Bis(diphenylphosphino)-2,2′,3,3′-tetrahydro-5,5′-bi-1,4-           benzodioxin; (S)-SYNPHOS TM;       80499-19-0   1,4-Bis(di-i-propylphosphino)butane;           1,2-Bis(di-4-sulfonatophenylphosphino)benzene tetrasodium salt DMSO           adduct           (R)-(−)-4,12-Bis(di(3,5-xylyl)phosphino)-[2.2]-paracyclophane; CTH-           (R)-3,5-xylyl-PHANEPHOS;           (S)-(+)-4,12-Bis(di(3,5-xylyl)phosphino)-[2.2]-paracyclophane; CTH-           (S)-3,5-xylyl-PHANEPHOS;       36802-41-2   Bis(2-methoxyphenyl)phenylphosphine;       28240-66-6   1,3-Bis(phenylphosphino)propane;       151888-20-9   Bis(p-sulfonatophenyl)phenylphosphine dihydrate dipotassium salt;       65013-26-5   Bis(triphenylphosphine)iminium borohydride;       21050-13-5   Bis(triphenylphosphine)iminium chloride;       321921-71-5   Butyldi-1-adamantylphosphine; [cataCXium A];       93634-87-8   t-Butyldicyclohexylphosphine;       6372-42-5   Cyclohexyldiphenylphosphine;       822-68-4   Cyclohexylphosphine;       131211-27-3   Di-1-adamantylphosphine;       126683-99-6   Di-1-adamantylphosphinic chloride;       138517-61-0   (1R,2R)-(+)-1,2-Diaminocyclohexane-N,N′-bis(2′-           diphenylphosphinobenzoyl); TROST LIGAND;       174810-09-4   (1R,2R)-(+)-1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphino-1-           naphthoyl); TROST LIGAND (NAPHTHYL);       205495-66-5   (1S,2S)-(−)-1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphino-1-           naplthoyl); TROST LIGAND (NAPHTHYL);       13716-10-4   Di-t-butylchlorophosphine;           Di-t-butylcyclohexylphosphine;       6002-40-0   Di-t-butylmethylphosphine;       4006-38-6   Di-i-butylphosphine;       255836-67-0   racemic-2-Di-t-butylphosphino-1,1′-binaphthyl;       224311-51-7   2-(Di-t-butylphosphino)biphenyl;       224311-49-3   2-Di-t-butylphosphino-2′-(N,N-dimethylamino)biphenyl;       360577-23-7   [2-(Di-t-butylphosphino)ethyl]trimethylammonium chloride;       255837-19-5   2-Di-t-butylphosphino-2′-methylbiphenyl;       1809-19-4   Di-n-butylphosphite;       185913-97-7   (R)-(+)-5,5′-Dichloro-6,6′-dimethoxy-2,2′-bis(diphenylphosphino)-1,1′-           biphenyl; (R)-Cl-MeO-BIPHEP;       185913-98-8   (S)-(−)-5,5′-Dichloro-6,6′-dimethoxy-2,2′-bis(diphenylphosphino)-1,1′-           biphenyl; (S)-Cl-MeO-BIPHEP;       247940-06-3   2-(Dicyclohexylphosphino)biphenyl;           2-Dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl; S-PHOS;       213697-53-1   2-(Dicyclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl;       181864-78-8   [2-(Dicyclohexylphosphino)ethyl]trimethylammonium chloride;       251320-86-2   2-Dicyclohexylphosphino-2′-methylbiphenyl;       564483-18-7   2-(Dicyclohexylphosphino)-2′,4′,6′-tri-i-Propyl-1,1′-biphenyl; X-PHOS;       39864-68-1   Dicyclopentylphosphine;       627-49-6   Diethylphosphine;       762-04-9   Diethylphosphite;       21302-09-0   Dilauryl hydrogen phosphite;       161265-03-8   9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene; XANTPHOS;       672-66-2   Dimethylphenylphosphine;       148432-44-4   Di-2-norbornylphosphine;       1499-21-4   Diphenylphosphinic chloride;       186803-02-1   (1R,1′R,2R,2′R)-(−)-2,2′-Diphenylphosphino-1,1′-bicyclopentyl; (R,R)-           BICP;           (1S,1′S,2S,2′S)-(+)-2,2′-Diphenylphosphino-1,1′-bicyclopentyl; (S,S)-           BICP;       240417-00-9   2-Diphenylphosphino-2′-(N,N-dimethylamino)biphenyl;       145964-33-6   (R)-(+)-2-(Diphenylphosphino)-2′-methoxy-1,1′-binaphthyl; (R)-MOP;       134484-36-9   (S)-(−)-2-(Diphenylphosphino)-2′-methoxy-1,1′-binaphthyl; (S)-MOP;       132682-77-0   2-Diphenylphosphino-6-methylpyridine;       149341-34-4   (R)-(+)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline (R)-QUINAP       149341-33-3   (S)-(−)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline (S)-QUINAP;       164858-78-0   (R)-(+)-2-[2-(Diphenylphosphino)phenyl]-4-(1-methylethyl)-4,5-           dihydrooxazole;       1809-20-7   Di-i-propylphosphite;       1017-60-3   Di-p-tolylphosphine;       607-01-2   Ethyldiphenylphosphine;       15715-41-0   Methyldiethoxyphosphine;       1486-28-8   Methyldiphenylphosphine;       43077-29-8   (S)-(+)-Neomenthyldiphenylphosphine (S)-NMDPP;       824-72-6   Phenyldichlorophosphine oxide;           N-Phenyl-2-(di-t-butylphosphino)pyrrole; [cataCXium PtB];           N-Phenyl-2-(dicyclohexylphosphino)pyrrole; [cataCXium PCy];       2946-61-4   Phenyldimethoxyphosphine;       1779-48-2   Phenylphosphinic acid;       15573-31-6   n-Propyldichlorophosphine;       362524-23-0   (S)-(−)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-           bipyridine; CTH-(S)-P-PHOS;       442905-33-1   (R)-(+)-2,2′,6,6′-Tetramethoxy-4,4′-bis(di(3,5-xylyl)phosphino)-3,3′-           bipyridine; CTH-(R)-Xylyl-P-Phos;       3676-97-9   Tetramethylbiphosphine disulfide;       1031-93-2   p-Tolyldiphenylphosphine;       16523-89-0   Triallylphosphine;       4125-25-1   Tri-i-butylphosphine;       13716-12-6   Tri-t-butylphosphine;       102-85-2   Tri-n-butylphosphite;       29949-85-7   Tri(m-chlorophenyl)phosphine;       1159-54-2   Tri(p-chlorophenyl)phosphine;       7650-88-6   Tricyclopentylphosphine;       554-70-1   Triethylphosphine;       122-52-1   Triethylphosphite;       594-09-2   Trimethylphosphine;       82164-75-8   2,4,4-Trimethylpentylphosphine;       594-09-2   Trimethylphosphine;       3411-48-1   Tri(1-naphthyl)phosphine;       14540-52-4   Tri-neo-pentylphosphite;       4731-53-7   Tri-n-octylphosphine; TOP;       101-02-0   Triphenylphosphite;       6476-36-4   Tri-i-propylphosphine,       2234-97-1   Tri-n-propylphosphine;       116-17-6   Tri-i-propylphosphite;       51805-45-9   Tris(2-carboxyethyl)phosphine, hydrochloride;       4023-53-4   Tris(2-cyanoethyl)phosphine;       31570-04-4   Tris(2,4-di-t-butylphenyl)phosphite;       443150-11-6   Tris(4,6-dimethyl-3-sulfanatophenyl)phosphine trisodium salt hydrate;       28926-65-0   1,1,1-Tris(diphenylphosphino)methane;       22031-12-5   1,1,1-Tris(diphenylphosphinomethyl)ethane;       2767-80-8   Tris(hydroxymethyl)phosphine;       4706-17-6   Tris(hydroxypropyl)phosphine;       121898-64-4   Tris(4-methoxy-3,5-dimethylphenyl)phosphine;       4731-65-1   Tris(o-methoxyphenyl)phosphine;       29949-84-6   Tris(m-methoxyphenyl)phosphine;       1259-35-4   Tris(pentafluorophenyl)phosphine;       63995-70-0   Tris(3-sulfonatophenyl)phosphine hydrate;       13406-29-6   Tris(p-trifluoromethylphenyl)phosphine;       91608-15-0   Tris (2,4,6-trimethoxyphenyl)phosphine;       15573-38-3   Tris(trimethylsilyl)phosphine;       6224-63-1   Tri-m-tolylphosphine;       2155-96-6   Vinyldiphenylphosphine;       60648-70-6   Bis(tri-t-butylphosphine)platinum (O);       15692-07-6   cis-Dichlorobis(triethylphosphine)platinum (II);       15604-36-1   cis-Dichlorobis(triphenylphosphine)platinum (II);       19529-53-4   Tetrakis(trifluorophosphine)platinum (0) (ampouled under PF3);       23032-93-1   Iododioxobis(triphenylphosphine)rhenium (V);       154661-57-1   (2S,4S)-(−)-2,4-Bis(diphenylphosphino)pentane(norbornadiene)rhodium           (I) hexafluorophosphate;       157772-65-1   1,1′-Bis(di-i-propylphosphino)ferrocene(1,5-cyclooctadiene)rhodium (I)           tetrafluoroborate;       13938-94-8   Chlorocarbonylbis(triphenylphosphine)rhodium (I);       17185-29-4   Hydridocarbonyltris(triphenylphosphine)rhodium (I);       25360-32-1   Carbonyl(dihydrido)tris(triphenylphosphine)ruthenium (II);           Chloro[(R)-(+)-5,5′-dichloro-6,6′-dimethoxy-2,2′-           bis(diphenylphosphino)-1,1′-biphenyl](p-cymene)ruthenium (II) chloride           CH2C12 adduct;           Chloro[(S)-(−)-5,5′-dichloro-6,6′-dimethoxy-2,2′-bis(diphenylphosphino)-           1,1′-biphenyl](p-cymene)ruthenium (II) chloride CH2C12 adduct;       141686-21-7   Chloro[hydrotris(pyrazol-1-yl)borato]bis(triphenylphosphine)ruthenium           (II) ethanol adduct;       99897-61-7   Chloro(indenyl)bis(triphenylphosphine)ruthenium (II), dichloromethane           adduct;       329735-86-6   Dichloro[(R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl][(2R)-(−)-           1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]ruthenium (II);       329735-87-7   Dichloro[(S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl][(1R,2R)-           (+)-1,2-diphenylethylenediamine]ruthenium (II);       329736-05-2   Dichloro[(S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl][(1S,2S)-(−)-           1,2-diphenylethylenediamine]ruthenium (II);       325150-57-0   Dichloro[(R)-(−)-4,12-bis(di(3,5-xylyl)phosphino)-[2.2]-           paracyclophane][(1S,2S)-(−)-1,2-diphenylethylenediamine]ruthenium (II);       14564-35-3   Dichlorodicarbonylbis(triphenylphosphine)ruthenium (II);       148630-66-4   Trimethylphosphine(hexafluoroacetylacetonato)silver (I);       82149-18-6   Sodium(cyclopentadienyl)tris(dimethylphosphito)cobaltate (I);       10039-56-2   Sodium hypophosphite monohydrate;           [[(2S,3S,5S,6S)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2,3-           diyl]bis(methylene)]bis[diphenyl-Phosphine           [[(2R,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2,3-           diyl]bis(methylene)]bis[diphenyl-Phosphine           1,1″-[(1R,2R)-1,2-cyclohexanediylbis(iminocarbonyl)]bis[2-           (diphenylphosphino)-, (2R,2″R)-Ferrocene           1,1″-[(1S,2S)-1,2-cyclohexanediylbis(iminocarbonyl)]bis[2-           (diphenylphosphino)-, (2S,2″S)-Ferrocene           2,5-bis[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]-1,2,5,6-           tetradeoxy-3,4-O-(1-methylethylidene)-D-Mannitol           2,5-bis[bis[3,5-dimethylphenyl)phosphino]-1,2,5,6-tetradeoxy-3,4-O-(1-           methylethylidene)-D-Mannitol           Phosphinous acid, diphenyl-, (1S)-3,3′-diphenyl[1,1′-binaphthalene]-2,2′-           diyl ester           Phosphinous acid, diphenyl-, (1R)-3,3′-diphenyl[1,1′-binaphthalene]-2,2′-           diyl ester           1,1′-bis(1,1-dimethylethyl)-, (1S,1′S,2R,2′R)-2,2′-Biphospholane           1,1′-bis(1,1-dimethylethyl)-, (1R,1′R,2S,2′S)-2,2′-Biphospholane           [(2,3,5,6-η)-bicyclo[2.2.1]hepta-2,5-diene][(1R,1′R,2R,2′R)-1,1′-bis(1,1-           dimethylethyl)-2,2′-biphospholane-κP1,κP1′]-, (OC-6-11)-Rhodium(1+)           hexafluoroantimonate(1−)           [(2,3,5,6-η)-bicyclo[2.2.1]hepta-2,5-diene][(1R,1′R,2R,2′R)-1,1′-bis(1,1-           dimethylethyl)-2,2′-biphospholane-κP1,κP1′]-Rhodium(1+)           [1,1′-bis[(3aS,4S,6S,6aS)-tetrahydro-2,2,4,6-tetramethyl-5H-           phospholo[3,4-d]-1,3-dioxol-5-yl-κP5]ferrocene][(1,2,5,6-η)-1,5-           cyclooctadiene]-, hexafluorophosphate(1−) Rhodium(1+)           [1,1′-bis[(3aS,4S,6S,6aS)-tetrahydro-2,2,4,6-tetramethyl-5H-           phospholo[3,4-d]-1,3-dioxol-5-yl-κP5]ferrocene][(1,2,5,6-η)-1,5-           cyclooctadiene]-Rhodium(1+)           1,1′-bis[(3aS,4S,6S,6aS)-tetrahydro-2,2,4,6-tetramethyl-5H-           phospholo[3,4-d]-1,3-dioxol-5-yl]-Ferrocene           1,1′-bis[(3aS,4S,6S,6aS)-tetrahydro-2,2-dimethyl-4,6-bis(phenylmethyl)-           5H-phospholo[3,4-d]-1,3-dioxol-5-yl]-Ferrocene           1,1′-bis[(3aS,4S,6S,6aS)-4,6-diethyltetrahydro-2,2-dimethyl-5H-           phospholo[3,4-d]-1,3-dioxol-5-yl]-Ferrocene,           1,1′-bis[(11bS)-3,5-dihydro-4H-dinaphtho[2,1-c:1′,2′-e]phosphepin-4-yl]-           Ferrocene           1,1′-bis[(11bR)-3,5-dihydro-4H-dinaphtho[2,1-c:1′,2′-e]phosphepin-4-yl]-           Ferrocene,           3,3′-Bi-3H-dinaphtho[2,1-c:1′,2′-e]phosphepin, 4,4′-bis(1,1-           dimethylethyl)-4,4′,5,5′-tetrahydro-, (3S,3′S,4S,4′S,11bS,11′bS)-           [(1″S)-4′,4″,5′,5″,6′,6″-hexamethoxy[1,1′:3′,1″:3″,1′′′-quaterphenyl]-2′,2″-           diyl]bis[diphenyl-Phosphine           5,5′-(1,2-phenylene)bis[tetrahydro-2,2,4,6-tetramethyl-,           (3aS,3′aS,4R,4′R,6R,6′R,6aS,6′aS)-5H-Phospholo[3,4-d]-1,3-dioxole           5,5′-(1,2-phenylene)bis[tetrahydro-2,2,4,6-tetramethyl-,           (3aS,3′aS,4S,4′S,6S,6′S,6aS,6′aS)-5H-Phospholo[3,4-d]-1,3-dioxole           5,5′-(1,2-phenylene)bis[tetrahydro-2,2-dimethyl-4,6-bis(phenylmethyl)-           5H-Phospholo[3,4-d]-1,3-dioxole           5,5′-(1,2-phenylene)bis[tetrahydro-2,2-dimethyl-4,6-bis(3-methylbutyl)-           5H-Phospholo[3,4-d]-1,3-dioxole           5,5′-(1,2-phenylene)bis[tetrahydro-2,2-dimethyl-4,6-dipropyl-5H-           Phospholo[3,4-d]-1,3-dioxole           5,5′-(1,2-phenylene)bis[4,6-diethyltetrahydro-2,2-dimethyl-,           (3aS,3′aS,4S,4′S,6S,6′S,6aS,6′aS)-5H-Phospholo[3,4-d]-1,3-dioxole           4,4′-(1,2-phenylene)bis[4,5-dihydro-, (11bS,11′bS)-3H-Dinaphtho[2,1-           c:1′,2′-e]phosphepin           4,4′-(1,2-phenylene)bis[4,5-dihydro-, (11bR,11′bR)-3H-Dinaphtho[2,1-           c:1′,2′-e]phosphepin           Ruthenate(1−), tri-μ-chlorodichlorobis[(11aS)-dibenzo[d,f][1,3]dioxepin-           1,11-diylbis[diphenylphosphine-κP]]di-, hydrogen, compd. with N-           methylmethanamine (1:1)           Ruthenate(1−), tri-μ-chlorodichlorobis[(11aS)-dibenzo[d,f][1,3]dioxepin-           1,11-diylbis[diphenylphosphine-κP]]di-, hydrogen           (11aS)-dibenzo[d,f][1,3]dioxepin-1,11-diylbis[diphenyl-Phosphine           (11aR)-dibenzo[d,f][1,3]dioxepin-1,11-diylbis[diphenyl-Phosphine           Ruthenate(1−), tri-μ-chlorodichlorobis[[(12aS)-6,7-           dihydrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenylphosphine-           κP]]di-, hydrogen, compd. with N-methylmethanamine (1:1)           Ruthenate(1−), tri-μ-chlorodichlorobis[[(12aS)-6,7-           dihydrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenylphosphine-           κP]]di-, hydrogen,           [(12aS)-6,7-dihydrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenyl-           Phosphine           [(12aR)-6,7-dihydrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenyl-           Phosphine           [(13aS)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin-1,13-           diyl]bis[diphenyl-Phosphine           [(13aR)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin-1,13-           diyl]bis[diphenyl-Phosphine           [(14aS)-6,7,8,9-tetrahydrodibenzo[b,d][1,6]dioxecin-1,14-           diyl]bis[diphenyl-Phosphine           [(14aR)-6,7,8,9-tetrahydrodibenzo[b,d][1,6]dioxecin-1,14-           diyl]bis[diphenyl-Phosphine           [(15aR)-7,8,9,10-tetrahydro-6H-dibenzo[b,d][1,6]dioxacycloundecin-           1,15-diyl]bis[diphenyl-Phosphine           [(15aS)-7,8,9,10-tetrahydro-6H-dibenzo[b,d][1,6]dioxacycloundecin-           1,15-diyl]bis[diphenyl-Phosphine           [(16aR)-6,7,8,9,10,11-hexahydrodibenzo[b,d][1,6]dioxacyclododecin-           1,16-diyl]bis[diphenyl-Phosphine           [(16aS)-6,7,8,9,10,11-hexahydrodibenzo[b,d][1,6]dioxacyclododecin-           1,16-diyl]bis[diphenyl-Phosphine                  
 
         [0035]     In another embodiment, the present invention provides a composition comprising a compound selected from Table 1 and paraffin.