Datasets:

starling-labs
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Reactions

PMID int64 37 41.1M	pmid large_stringlengths 2 8	support_text large_stringlengths 23 2.28k	reaction_type large_stringlengths 2 119 ⌀	reactants large_stringlengths 1 453 ⌀	product large_stringlengths 1 724	reagent large_stringlengths 1 267 ⌀	catalyst large_stringlengths 1 325 ⌀	solvent large_stringlengths 1 263 ⌀	yield_percent float64 0 11.7k ⌀	yield_type large_stringclasses 8 values	outcome_status large_stringclasses 5 values	temperature large_stringlengths 1 85 ⌀	reaction_time large_stringlengths 1 180 ⌀	setup_and_notes large_stringlengths 1 443 ⌀	extra_details large_stringlengths 3 349 ⌀	product_smiles large_stringlengths 1 1.53k
38,279,298	38279298	Zu and Kinjo investigated the regioselective cycloaddition involving 1,2-diboraallene 25 and azide, without catalysis and using mild conditions, leading to diboratriazole 26.	cycloaddition	1,2-diboraallene 25, azide	diboratriazole 26	null	null	null	null	null	success	null	null	without catalysis, mild conditions	null	B1=NN=NB1
21,506,178	21506178	The coupling of 2-chloropyridine with the N⁹-p-methoxybenzyl (PMB)-protected adenine 55 gave rise to 8-pyridyladenine 56 in 55% yield using a Pd(OH)₂/CuI system in combination with Cs₂CO₃ as the base.	heteroarylation	2-chloropyridine, N⁹-p-methoxybenzyl (PMB)-protected adenine 55	8-pyridyladenine 56	Cs₂CO₃	Pd(OH)₂/CuI	null	55	unspecified	success	null	null	null	null	Nc1ncnc2nc(-c3ccccn3)[nH]c12
17,525,926	17525926	6-(2-Dimethylaminonaphthoyl)alanine (DANA) was prepared by Imperiali and co-workers through the asymmetric alkylation of 2 with α-bromo ketone 81 and 17e as a phase-transfer catalyst.	alkylation	2, α-bromo ketone 81	6-(2-Dimethylaminonaphthoyl)alanine	null	17e	null	null	null	success	null	null	Asymmetric alkylation utilizing a phase-transfer catalyst.	null	CCN(CC)N=O
11,848,980	11848980	Whitehurst and collaborators showed that the condensation of 2-methylcyclopentane-1,3-dione (49) with methyl vinyl ketone gave 4-hydroxy-1,4-dimethylbicyclo[3.2.1]octane-7,8-dione (50) as a byproduct.	condensation	2-methylcyclopentane-1,3-dione, methyl vinyl ketone	4-hydroxy-1,4-dimethylbicyclo[3.2.1]octane-7,8-dione	null	null	null	null	null	success	null	null	obtained as byproduct	null	CC12CCC(C)(O)C(CC1=O)C2=O
15,186,185	15186185	Treatment of allyl phenyl ether... produced o-allylphenol almost quantitatively... Similar results were attained in the presence of ethylaluminum dichloride.	aromatic Claisen rearrangement	allyl phenyl ether	o-allylphenol	ethylaluminum dichloride	null	hexane	null	quantitative	success	room temperature	null	null	null	C=CCC1(O)C=CC=CC1
12,744,695	12744695	After activation of the resulting allylic alcohol as the carbonate 235, the nitroacetic acid ethyl ester was introduced under palladium catalysis. 236, the precursor of (±)- carbovir, was isolated in quantitative yield.	cross-coupling	carbonate 235, nitroacetic acid ethyl ester	236	null	palladium	null	null	quantitative	success	null	null	null	null	O=C([O-])C[N+](=O)[O-]
30,875,202	30875202	The ZnI₂-catalyzed reaction of chiral nitorone 2 with silyl ketene acetal gives methyl (2S,3R)-[1,3-bis(tert-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate in a 90:10 trans/cis ratio.	Mannich-type addition	nitorone 2, silyl ketene acetal	methyl (2S,3R)-[1,3-bis(tert-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate	null	ZnI₂	null	null	null	success	null	null	Product obtained in a 90:10 trans/cis ratio.	null	COC(=O)C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)CCN1O[Si](C)(C)C(C)(C)C
19,831,366	19831366	Application of a modified Polonovski reaction for serratinine 244 resulted in generation of serratezomine A 245.	Polonovski reaction	serratinine	serratezomine A	null	null	null	null	null	success	null	null	Modified Polonovski reaction.	null	C[C@H]1C[C@@H]2OC(=O)C[C@H]([C@H]1O)[C@]21CCCN2CCC[C@@H]21
17,488,063	17488063	Subsequent multistep reduction with LiAlH₄ gave a tetrol, which was cyclized to the final product (-)-eudesmin (26) by dehydration again using BF₃·OEt₂.	cyclization	tetrol	(-)-eudesmin (26)	null	BF₃·OEt₂	null	null	null	success	null	null	dehydration step	null	COc1ccc([C@@H]2OC[C@@H]3[C@H]2CO[C@H]3c2ccc(OC)c(OC)c2)cc1OC
27,018,601	27018601	Cyclobutene rac-328 was quantitatively obtained from maleic anhydride and propargyl alcohol upon irradiation of a MeCN solution in the presence of acetophenone.	[2 + 2] photocycloaddition	maleic anhydride, propargyl alcohol	cyclobutene rac-328	acetophenone	null	MeCN	null	quantitative	success	null	null	irradiation	null	C1=CCC1
17,410,611	17410611	treatment of 146 with HCl resulted in the formation of [{(IPr)PdCl2}2] (110).	substitution	compound 146, HCl	[{(IPr)PdCl2}2]	null	null	null	null	null	success	null	null	null	null	[Cl][Pd][Cl]
36,677,727	36677727	3-Nitro-4-(trichloromethyl)pyrrolidine 30 was obtained through the cycloaddition of trans-3,3,3-trichloro-1-nitroprop-1-ene 29 with azomethine ylide (obtained from the condensation of paraformaldehyde and sarcosine in refluxing benzene).	cycloaddition	trans-3,3,3-trichloro-1-nitroprop-1-ene, paraformaldehyde, sarcosine	3-Nitro-4-(trichloromethyl)pyrrolidine	null	null	benzene	null	null	success	reflux	null	null	null	O=[N+]([O-])C1CNCC1C(Cl)(Cl)Cl
16,011,327	16011327	The N-arylation under solid-phase conditions was carried out in the presence of P(t-Bu)₃ and Cy₂NMe in toluene at 80 °C when it involved the substitution of the C-N bond for a C-Br bond for the intramolecular cyclization of immobilized α-acetamidoβ-(o-bromophenyl)acrylates.	Buchwald/Hartwig intramolecular N-arylation	immobilized α-acetamidoβ-(o-bromophenyl)acrylates	indole	Cy₂NMe	Pd₂(dba)₃, P(t-Bu)₃	toluene	null	null	success	80 °C	null	Solid-phase synthesis; substitution of C-N bond for C-Br bond.	null	c1ccc2[nH]ccc2c1
21,506,178	21506178	Furan-2-carboxylic acid was monoarylated regioselectively, whereas 3-furancarboxylic acid did not lead to any of the desired product.	decarboxylative cross-coupling	3-furancarboxylic acid	desired product	null	null	null	0	unspecified	failed	null	null	null	null	O=C(O)c1ccoc1
18,072,806	18072806	6-(2-Dimethylaminonaphthoyl)alanine (DANA) was prepared by Imperiali through the asymmetric alkylation of 2 with α-bromoketone 54 using 19e as a phase-transfer catalyst.	asymmetric alkylation	2, α-bromoketone 54	6-(2-Dimethylaminonaphthoyl)alanine	null	19e	null	null	null	success	null	null	null	null	CCN(CC)N=O
19,831,366	19831366	A catalytic enantioselective [4 + 2] cycloaddition of cyclopentadiene 2 with propirolamide derivative 17a yielded bridged cycloadduct 18 with 50% yield and 93% ee at -78 °C.	cycloaddition	cyclopentadiene 2, propirolamide derivative 17a	bridged cycloadduct 18	null	null	null	50	unspecified	success	-78 °C	null	null	93% ee	C1=CCC=C1
19,831,366	19831366	A catalytic enantioselective [4 + 2] cycloaddition of cyclopentadiene 2 with propirolamide derivative 17a yielded bridged cycloadduct 18 with 91% yield and 88% ee at -40 °C.	cycloaddition	cyclopentadiene 2, propirolamide derivative 17a	bridged cycloadduct 18	null	null	null	91	unspecified	success	-40 °C	null	null	88% ee	C1=CCC=C1
17,525,926	17525926	High levels of enantioselectivity can be obtained by performing the asymmetric Michael addition of glycine diphenylmethyl ester Schiff base 51 to simple alkyl vinyl ketones, such as methyl vinyl ketone, in diisopropyl ether at 0 °C in the presence of 50 mol % Cs₂CO₃ and 1 mol % ent-50 as the catalyst.	Michael addition	glycine diphenylmethyl ester Schiff base 51, methyl vinyl ketone	methyl vinyl ketone adduct	Cs₂CO₃	ent-50	diisopropyl ether	null	null	success	0 °C	null	50 mol % Cs₂CO₃, 1 mol % ent-50	null	C=CC(C)=O
23,082,820	23082820	the 1,3-cis-difunctionalized cyclopentane 89 or its bicyclic lactol 90a, when treated with 5 mol% of Fe(CO)₅, smoothly evolved to the expected bridged hydroxy ketone 91 as the only observed diastereomer.	domino isomerization–intramolecular aldolization	compound 89, compound 90a	4-hydroxy-bicyclo[3.2.1]octan-2-one	null	Fe(CO)₅	null	null	unspecified	success	null	null	5 mol% catalyst used.	null	O=C1CC(O)C2CCC1C2
11,848,752	11848752	Isomünchnones derived from the Rh2(OAc)4-catalyzed reaction of acyclic diazo imides 150–154 underwent facile cycloaddition onto the tethered π-bond to provide polycyclic adducts 155–159.	1,3-dipolar cycloaddition	acyclic diazo imides 150–154	polycyclic adducts 155–159	null	Rh2(OAc)4	null	null	null	success	null	null	Tandem reaction involving formation of isomünchnone followed by intramolecular cycloaddition.	null	CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Rh+3].[Rh+3]
11,848,752	11848752	Treatment of cyclic diazo imides 160–162 with Rh2(OAc)4 led to good yields of cycloadducts 163-165.	1,3-dipolar cycloaddition	cyclic diazo imides 160–162	cycloadducts 163-165	null	Rh2(OAc)4	null	null	unspecified	success	null	null	Tandem reaction involving formation of isomünchnone followed by intramolecular cycloaddition.	null	CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Rh+3].[Rh+3]
25,337,795	25337795	The Pd-catalyzed amidation of 2b to the amidation product 3b was performed using 2 mol% Pd(OAc)₂ and 4 mol% XPhos, with 2.2 equivalents of K₂CO₃ in Dioxane MeOH at 90 °C for 20 h.	amidation	2b	3b	K2CO3	Pd(OAc)2, XPhos	Dioxane, MeOH	null	null	success	90 °C	20 h	2.2 equiv K2CO3	null	CS(=O)(=O)N1CC(c2ccccc2)=Cc2ccccc21
35,423,221	35423221	Hekmati and co-workers used pramipexole–MWCNTs/palladium as a phosphine-free reusable heterogeneous catalyst for the Sonogashira coupling reaction of a wide range of aryl halides (including aryl bromides, iodides, and chlorides) with phenylacetylene.	Sonogashira coupling	aryl halides, phenylacetylene	corresponding products	null	pramipexole–MWCNTs/Pd	null	null	unspecified	success	null	null	Phosphine-free reusable heterogeneous catalyst.	null	C#Cc1ccccc1
12,744,695	12744695	Ammonolyzis and glycosylation of the 4'-OMe analogues 263a-c afforded the desired 8-aza-7-deazaadenine (264c).	ammonolyzis, glycosylation	263c	8-aza-7-deazaadenine (264c)	null	null	null	null	null	success	null	null	null	null	Nc1ncnc2c1CN=N2
12,744,695	12744695	Whale et al. reported the palladium-catalyzed Heck reaction of 5-iodouridine (52) with esters of acrylic acid to generate a series of esters of the acid (E)-5-(2-carboxyvinyl)uridine (97a–r) in poor to moderate yield.	Heck reaction	5-iodouridine, esters of acrylic acid	(E)-5-(2-carboxyvinyl)uridine	null	palladium	null	null	unspecified	success	null	null	yield was poor to moderate	null	O=C(O)/C=C/c1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O
25,635,524	25635524	This photocatalyzed reaction was performed by irradiation of a mixture of the steroidal dienones with trifluoromethyl iodide in the presence of pyridine with ultraviolet light (3500 Å) at room temperature, however, the yields were low (32–42%).	trifluoromethylation	steroidal dienones, trifluoromethyl iodide	α-trifluoromethylated enones	pyridine	null	null	37	unspecified	success	room temperature	null	irradiation with ultraviolet light (3500 Å); yield range 32-42%	null	FC(F)(F)I
17,091,931	17091931	Benzo[4,5]furopyridine (538) can be obtained in a 64% yield by the cross-coupling of diaryl ether 537, when catalyzed by Pd(OAc)₂ under ligand-free conditions.	cross-coupling	diaryl ether 537	benzo[4,5]furopyridine	null	Pd(OAc)₂	null	64	unspecified	success	null	null	ligand-free conditions	null	c1ccc2c(c1)oc1cccnc12
11,848,917	11848917	By the addition of 150 mol % of ZnI₂, the reaction of cyclic nitrone 57 and alkene 133 gives endo-135 as the major isomer with a yield of 82% and a reaction time of 48 h at 35 °C.	1,3-dipolar cycloaddition	compound 57, compound 133	compound 135	ZnI₂	null	null	82	unspecified	success	35 °C	48 h	150 mol % ZnI₂ used; endo:exo ratio improved to 89:11; diastereofacial selectivity improved to 92% de.	null	[I-].[I-].[Zn+2]
11,848,917	11848917	The reaction of 2-[(trimethylsilyl)oxy]furan 143 with chiral nitrones 144 catalyzed by stoichiometric amounts of an activator such as (+)- or (−)-(1pc)₂BOTf gives 145a as the major stereoisomer.	formal 1,3-dipolar cycloaddition	2-[(trimethylsilyl)oxy]furan, compound 144	compound 145a	(+)- or (−)-(1pc)₂BOTf	null	null	null	null	success	null	null	Stoichiometric amounts of activator used; high endo selectivity and diastereofacial selectivity up to 96% de.	null	C[Si](C)(C)Oc1ccco1
11,848,917	11848917	When TMSOTf is used as the catalyst, the reaction of 2-[(trimethylsilyl)oxy]furan 143 with chiral nitrones 144 proceeds via route B to give the butenolide 148 as the product.	formal 1,3-dipolar cycloaddition	2-[(trimethylsilyl)oxy]furan, compound 144	compound 148	null	TMSOTf	null	null	null	success	null	null	Reaction proceeds via intermediate 146 and route B.	null	C[Si](C)(C)OS(=O)(=O)C(F)(F)F
15,991,198	15991198	The final step of the total synthesis of rapamycin involved a double Stille coupling process and proceeded from the naked precursor 72 and trans-1,2-distannyl ethylene 73, under the influence of [PdCl₂(MeCN)₂] (20 mol%) and iPr₂NEt as a dilute solution in DMF/THF at ambient temperature.	double Stille coupling	precursor 72, trans-1,2-distannyl ethylene 73	rapamycin (76)	iPr₂NEt	[PdCl₂(MeCN)₂]	DMF/THF	null	null	success	ambient temperature	null	20 mol% [PdCl₂(MeCN)₂], dilute solution	null	CO[C@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)C[C@@H]2CC[C@@H](O)[C@H](OC)C2)CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C/1C
11,848,752	11848752	When rhodium(II) acetate was used as the catalyst [for α-diazo ketone 338], cyclopropane 339 was not formed.	carbenoid addition	α-diazo ketone 338	cyclopropane 339	null	rhodium(II) acetate	null	0	unspecified	failed	null	null	null	null	C1CC1
11,709,863	11709863	the Pd₂(dba)₃·CHCl₃ + 8AsPh₃ completely failed to catalyze the reaction [of chloropurine 244 and Zn(CN)₂ (245)].	cross-coupling	compound 244, zinc cyanide	compound 246	AsPh₃	Pd₂(dba)₃·CHCl₃	NMP	0	unspecified	failed	90 °C	null	null	null	[C-]#N.[C-]#N.[Zn+2]
11,709,863	11709863	Treatment of boronate ester 247 and enantiopure organozinc reagent 248 with a Pd(OAc)₂/TFP catalyst system in benzene afforded a 50-55% yield of the desired product 249.	cross-coupling	compound 247, compound 248	compound 249	TFP	Pd(OAc)₂	benzene	52.5	unspecified	success	null	null	Yield reported as 50-55%.	null	N[C@@H](Cc1ccc(B(O)O)cc1)C(=O)O
36,080,422	36080422	Hiyama coupling reaction of iodobenzene 76 and phenyl trimethoxysilane 8 resulted in 96% yield of biaryl product 92, catalyzed by Pd/ZnO nanoparticles using K2CO3 as the base in ethylene glycol under an air atmosphere at 100 °C.	Hiyama coupling	iodobenzene 76, phenyl trimethoxysilane 8	biaryl product 92	K2CO3	Pd/ZnO nanoparticles	ethylene glycol	96	unspecified	success	100 °C	null	air atmosphere	null	c1ccc(-c2ccccc2)cc1
36,080,422	36080422	The reaction of 4-methylphenylbromide 123 was performed with phenyl trimethoxysilane 8 using PS-PdONPs (1.5 mol%) catalyst, TBAC in aqueous NaOH solution at 80 °C under aerobic conditions for 3 h, which afforded 4-methylbiphenyl 79 in 88% yield.	Hiyama coupling	4-methylphenylbromide 123, phenyl trimethoxysilane 8	4-methylbiphenyl 79	TBAC, NaOH	PS-PdONPs	aqueous NaOH solution	88	unspecified	success	80 °C	3 h	aerobic conditions, 1.5 mol% catalyst	null	Cc1ccc(-c2ccccc2)cc1
36,080,422	36080422	The catalytic effect of PS-PdNPs on the Hiyama coupling reaction was observed, and it was noticed that the desired coupled product was not attained, but 4,4′-dimethylbiphenyl 124, the Ullmann coupling product, was afforded in 99% yield.	Ullmann coupling	4-methylphenylbromide 123	4,4′-dimethylbiphenyl 124	TBAC, NaOH	PS-PdNPs	aqueous NaOH solution	99	unspecified	success	80 °C	3 h	aerobic conditions; described as the result of a failed Hiyama coupling attempt	null	Cc1ccc(-c2ccc(C)cc2)cc1
36,080,422	36080422	The reaction of iodobenzene 76 with phenyl trimethoxysilane 8 using 4 mol% Pd(OAc)2 in 115 and CH3CN and 1-butyl-3-methylimidazolium fluoride [bmim]F at 70–120 °C for 8 h afforded the desired biphenyl derivative in 98% yield.	Hiyama cross-coupling	iodobenzene, phenyl trimethoxysilane	biphenyl derivative	1-butyl-3-methylimidazolium fluoride	Pd(OAc)2	CH3CN, 115	98	unspecified	success	70–120 °C	8 h	4 mol% Pd(OAc)2	null	Ic1ccccc1
36,080,422	36080422	The reaction of 11 with phenyltriethoxysilane 16 was carried out by utilizing Pd@M-SBA-15 (0.5 mol%) catalyst, acetic acid, and TBAF.3H2O in toluene at 100 °C in the air for 24 h resultantly afforded the corresponding biphenyl derivative 38 in 92% yield.	Hiyama cross-coupling	11, phenyltriethoxysilane	biphenyl derivative 38	acetic acid, TBAF.3H2O	Pd@M-SBA-15	toluene	92	unspecified	success	100 °C	24 h	in the air, 0.5 mol% catalyst	null	CC(=O)c1ccc(Br)cc1
27,018,601	27018601	Enantiomerically pure N-cinnamyl-4-vinyloxazolidin-2-one (31) underwent a highly diastereoselective [2 + 2] photocycloaddition to product 32.	[2 + 2] photocycloaddition	N-cinnamyl-4-vinyloxazolidin-2-one	32	null	Cu(I)	null	null	null	success	null	null	null	null	C=CC1COC(=O)N1CC=Cc1ccccc1
22,000,119	22000119	The procedure described at Section 4.5 was employed using 7b (0.10 g, 0.41 mmol), dry ammonium acetate (0.31 g, 4.10 mmol), 2d (0.13 g, 0.41 mmol), and dry methanol (5 mL) at 100 °C for 24 h to yield 36 mg (0.10 mmol, 26.1%) of 2-Phenyl-4-(pyridin-3-yl)-5,6-dihydrothieno[2,3-h]quinoline (33) as a white solid.	null	7b, 2d	2-Phenyl-4-(pyridin-3-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate	null	methanol	26.1	isolated	success	100 °C	24 h	36 mg isolated	null	c1ccc(-c2cc(-c3cccnc3)c3c(n2)-c2ccsc2CC3)cc1
22,000,119	22000119	The procedure described at Section 4.4 was employed using 6b (0.08 g, 0.34 mmol), dry ammonium acetate (0.26 g, 3.40 mmol), 2a (0.11 g, 0.34 mmol), and dry methanol (2.0 mL) at 100 °C for 12 h to yield 52 mg (45.4%) of 2-(Pyridin-2-yl)-4-(pyridin-3-yl)-5,6-dihydro-1,10-phenanthroline (14) as a white solid.	null	6b, 2a	2-(Pyridin-2-yl)-4-(pyridin-3-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	45.4	isolated	success	100 °C	12 h	52 mg isolated as a white solid	null	c1ccc(-c2cc(-c3cccnc3)c3c(n2)-c2ncccc2CC3)nc1
11,848,752	11848752	When a-diazo ketone 489a containing a terminal triple bond was treated with Rh₂(OAc)₄ in benzene with diallyl sulfide, cyclohexenone 492a was formed in 80% yield.	alkyne metathesis-ylide formation-sigmatropic rearrangement	compound 489a, diallyl sulfide	cyclohexenone 492a	null	Rh₂(OAc)₄	benzene	80	unspecified	success	null	null	null	null	O=C1C=CCCC1
11,848,752	11848752	Subjection of a-diazo ketone 489b (R = Ph) to the same reaction conditions [Rh₂(OAc)₄ in benzene with diallyl sulfide] gave cyclopentenone 492b as the exclusive product.	alkyne metathesis-ylide formation-sigmatropic rearrangement	compound 489b, diallyl sulfide	cyclopentenone 492b	null	Rh₂(OAc)₄	benzene	null	quantitative	success	null	null	exclusive product	null	O=C1C=CCC1
11,093,193	11093193	In the reaction of the isopropyl-substituted alkenylcarbene-chromium complex 270 with sterically demandingly substituted terminal alkynes such as 3,3-dimethylbutyne (271), the seven-membered heterocycle 274 was obtained as a byproduct.	[5+2] cocyclization	isopropyl-substituted alkenylcarbene-chromium complex 270, 3,3-dimethylbutyne	274	null	null	null	null	null	success	null	null	Product 274 was obtained as a byproduct in addition to acylcyclopentenones 272 and 273.	null	C1=CCCNC=C1
11,093,193	11093193	To favor formation of the dihydroazepine 274 possibly still further two equivalents of triphenylphosphane were added to the reaction mixture... Indeed, in this way the yield of 274 could be increased to 23%.	[5+2] cocyclization	isopropyl-substituted alkenylcarbene-chromium complex 270, 3,3-dimethylbutyne	274	triphenylphosphane	null	null	23	unspecified	success	null	null	Two equivalents of triphenylphosphane were added.	null	C1=CCCNC=C1
11,093,193	11093193	In the reaction of 270 with 182 in pyridine the product ratio was shifted towards the dihydroazepine 274, and at the same time under these conditions the tricarbonylchromium fragment was cleaved off. After purification by column chromatography the methylenepyrrolidine 276 was formed.	[5+2] cocyclization	270, 182	methylenepyrrolidine 276	null	null	pyridine	null	null	success	null	null	The reaction shifted towards dihydroazepine 274, but the tricarbonylchromium fragment was cleaved off, leading to 276 after purification by column chromatography.	null	C=C1CCCN1
22,000,119	22000119	The reaction of 7c (0.08 g, 0.35 mmol), dry ammonium acetate (0.27 g, 3.50 mmol), 2d (0.11 g, 0.35 mmol), and glacial acetic acid (0.5 mL) at 90 °C for 14 h yielded 25 mg (0.07 mmol, 20.7%) of 2-Phenyl-4-(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline (37) as a white solid.	null	7c, 2d	2-Phenyl-4-(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate	null	glacial acetic acid	20.7	isolated	success	90 °C	14 h	0.08 g 7c, 0.27 g ammonium acetate, 0.11 g 2d, 0.5 mL glacial acetic acid	null	c1ccc(-c2cc(-c3ccncc3)c3c(n2)-c2ccsc2CC3)cc1
27,960,274	27960274	Yamamoto et al. promoted these reactions by a combination of AgOTf (15 mol %) with BINAP (6 mol %) which led to the corresponding chiral β-hydroxy carbonyl compounds in enantioselectivities of up to 95% ee and moderate to good yields (33–83%).	aldol reaction	tributyltin enolates, aldehydes	chiral β-hydroxy carbonyl compounds	null	AgOTf, BINAP	null	83	unspecified	success	null	null	AgOTf 15 mol %, BINAP 6 mol %; yield range 33-83%	null	c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1
27,960,274	27960274	Yamamoto et al. developed an alternative asymmetric aldol reaction occurring between benzaldehyde and alkenyl trichloroacetate derived from cyclohexanone based on the same catalyst system using only 5 mol % of Bu3SnOMe, which resulted in the formation of the corresponding aldol product in 82% yield.	aldol reaction	benzaldehyde, alkenyl trichloroacetate derived from cyclohexanone	aldol product	Bu3SnOMe	AgOTf, BINAP	null	82	unspecified	success	null	null	5 mol % Bu3SnOMe	null	O=C1CCCCC1
27,960,274	27960274	In 2009, the same authors applied this catalyst system to the asymmetric aldol reactions of alkenyl trichloroacetates 1a–1c with α-ketoesters 2a–2d. The process was promoted by a combination of 20 mol % of AgOTf, 10 mol % of (R)-BINAP, and 8 mol % of Bu2Sn(OMe)2 in the presence of methanol as superstoichiometric additi...	aldol reaction	alkenyl trichloroacetates 1a–1c, α-ketoesters 2a–2d	aldol product	Bu2Sn(OMe)2, methanol	AgOTf, (R)-BINAP	THF	null	null	success	-20 °C	null	20 mol % AgOTf, 10 mol % (R)-BINAP, 8 mol % Bu2Sn(OMe)2, methanol as superstoichiometric additive	null	c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1
22,000,119	22000119	The procedure described at Section 4.4 was employed with 6c (0.08 g, 0.35 mmol), dry ammonium acetate (0.27 g, 3.50 mmol), 2d (0.11 g, 0.35 mmol), and dry methanol (2.5 mL) at 95 °C for 14 h to yield 70 mg (0.21 mmol, 60.2%) of 2-Phenyl-4-(pyridin-4-yl)-5,6-dihydro-1,10-phenanthroline (21) as a white solid.	null	6c, 2d	2-Phenyl-4-(pyridin-4-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	60.2	isolated	success	95 °C	14 h	70 mg isolated	null	c1ccc(-c2cc(-c3ccncc3)c3c(n2)-c2ncccc2CC3)cc1
22,000,119	22000119	The procedure described at Section 4.5 was employed using 7a (0.07 g, 0.30 mmol), dry ammonium acetate (0.23 g, 3.00 mmol), 2d (0.10 g, 0.30 mmol), and glacial acetic acid (0.5 mL) at 100 °C for 12 h to yield 52 mg (50.7%) of 2-Phenyl-4-(pyridin-2-yl)-5,6-dihydrothieno[2,3-h]quinoline (29) as an off-white solid.	null	7a, 2d	2-Phenyl-4-(pyridin-2-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate	null	glacial acetic acid	50.7	isolated	success	100 °C	12 h	52 mg isolated; product obtained as an off-white solid	null	c1ccc(-c2cc(-c3ccccn3)c3c(n2)-c2ccsc2CC3)cc1
22,000,119	22000119	The procedure described at Section 4.5 was used with 7b (0.10 g, 0.40 mmol), dry ammonium acetate (0.30 g, 4.00 mmol), 2a (0.13 g, 0.40 mmol), and dry MeOH (2.5 mL) at 90 °C for 21 h to yield 45 mg (32.3%) of 2-(Pyridin-2-yl)-4-(pyridin-3-yl)-5,6-dihydrothieno[2,3-h]quinoline (30) as a white solid.	null	7b, 2a	2-(Pyridin-2-yl)-4-(pyridin-3-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate	null	MeOH	32.3	isolated	success	90 °C	21 h	45 mg isolated; dry ammonium acetate and dry MeOH used.	null	c1ccc(-c2cc(-c3cccnc3)c3c(n2)-c2ccsc2CC3)nc1
22,000,119	22000119	The procedure described at Section 4.4 was employed with 6b (0.12 g, 0.50 mmol), dry ammonium acetate (0.38 g, 5.00 mmol), 2d (0.16 g, 0.50 mmol), and dry methanol (2.5 mL) at 100 °C for 12 h to yield 127 mg (0.38 mmol, 76.0%) of 2-Phenyl-4-(pyridin-3-yl)-5,6-dihydro-1,10-phenanthroline (17) as a white solid.	null	6b, 2d	2-Phenyl-4-(pyridin-3-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	76	isolated	success	100 °C	12 h	127 mg isolated	null	c1ccc(-c2cc(-c3cccnc3)c3c(n2)-c2ncccc2CC3)cc1
22,000,119	22000119	The procedure described at Section 4.4 was employed with 6c (0.07 g, 0.30 mmol), dry ammonium acetate (0.23 g, 3.00 mmol), 2a (0.10 g, 0.30 mmol), and dry methanol (2.5 mL) at 100 °C for 12 h to yield 41 mg (0.12 mmol, 40.6%) of 2-(Pyridin-2-yl)-4-(pyridin-4-yl)-5,6-dihydro-1,10-phenanthroline (18) as a white solid.	null	6c, 2a	2-(Pyridin-2-yl)-4-(pyridin-4-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	40.6	isolated	success	100 °C	12 h	41 mg isolated as a white solid	null	c1ccc(-c2cc(-c3ccncc3)c3c(n2)-c2ncccc2CC3)nc1
22,000,119	22000119	The reaction of 7c (0.05 g, 0.22 mmol) with dry ammonium acetate (0.17 g, 2.20 mmol) and 2b (0.07 g, 0.22 mmol) in glacial acetic acid (0.5 mL) at 100 °C for 14 h yielded 26 mg (34.6%) of 2-(Pyridin-3-yl)-4-(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline (35) as a white solid.	null	7c, 2b	2-(Pyridin-3-yl)-4-(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate	null	glacial acetic acid	34.6	isolated	success	100 °C	14 h	26 mg isolated	null	c1cncc(-c2cc(-c3ccncc3)c3c(n2)-c2ccsc2CC3)c1
22,000,119	22000119	Using the procedure from Section 4.5, 7a (0.06 g, 0.25 mmol), dry ammonium acetate (0.19 g, 2.50 mmol), 2b (0.08 g, 0.25 mmol), and glacial acetic acid (0.5 mL) were reacted at 100 °C for 20 h to yield 43 mg (51.6%) of 4-(Pyridin-2-yl)-2-(pyridin-3-yl)-5,6-dihydrothieno[2,3-h]quinoline (27) as a light yellow solid.	null	7a, 2b	4-(Pyridin-2-yl)-2-(pyridin-3-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate, glacial acetic acid	null	glacial acetic acid	51.6	isolated	success	100 °C	20 h	43 mg isolated; product obtained as a light yellow solid	null	c1ccc(-c2cc(-c3cccnc3)nc3c2CCc2sccc2-3)nc1
22,000,119	22000119	The procedure described at Section 4.4 was employed with 6a (0.09 g, 0.40 mmol), dry ammonium acetate (0.31 g, 4.00 mmol), 2b (0.13 g, 0.40 mmol), and dry methanol (2.5 mL) at 100 °C for 12 h to yield 92 mg (68.3%) of 11 as a white solid.	null	6a, 2b	4-(Pyridin-2-yl)-2-(pyridin-3-yl)-5, 6-dihydro-1, 10-phenanthroline	ammonium acetate	null	methanol	68.3	isolated	success	100 °C	12 h	92 mg isolated; 0.09 g of 6a and 0.13 g of 2b used	null	c1ccc(-c2cc(-c3cccnc3)nc3c2CCc2cccnc2-3)nc1
11,848,752	11848752	diazo ketone 589 was cleanly converted into methylene cyclooctene 590.	rearrangement	diazo ketone 589	methylene cyclooctene 590	null	null	null	null	unspecified	success	null	null	cleanly converted	null	C=C1C=CCCCCC1
22,000,119	22000119	The procedure described at Section 4.5 was employed with 7d (0.09 g, 0.37 mmol), dry ammonium acetate (0.28 g, 3.70 mmol), 2c (0.12 g, 0.37 mmol), and dry methanol (2.5 mL) at 100 °C for 36 h to yield 23 mg (0.06 mmol, 18.0%) of 4-Phenyl-2-(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline (40) as a white solid.	null	7d, 2c	4-Phenyl-2-(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate	null	methanol	18	isolated	success	100 °C	36 h	23 mg isolated	null	c1ccc(-c2cc(-c3ccncc3)nc3c2CCc2sccc2-3)cc1
22,000,119	22000119	Compound 38 (4-Phenyl-2-(pyridin-2-yl)-5,6-dihydrothieno[2,3-h]quinoline) was synthesized using 7d (0.12 g, 0.50 mmol), dry ammonium acetate (0.38 g, 5.00 mmol), 2a (0.16 g, 0.50 mmol), and dry methanol (5 mL) at 100 °C for 48 h, yielding 45 mg (26.6%) of the product as a white solid.	null	7d, 2a	4-Phenyl-2-(pyridin-2-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate	null	methanol	26.6	isolated	success	100 °C	48 h	45 mg isolated	null	c1ccc(-c2cc(-c3ccccn3)nc3c2CCc2sccc2-3)cc1
11,749,314	11749314	Palladium-catalyzed cyclization of vinylallene 458 in the presence of carbon monoxide provided a highly functionalized cyclononadienone 459.	cycloaddition	vinylallene 458, carbon monoxide	cyclononadienone 459	null	palladium	null	null	null	success	null	null	The reaction is described as a [4+4+1] cycloaddition.	null	O=C1C=CC=CCCCC1
22,000,119	22000119	A procedure described at Section 4.4 was used with 6a (0.08 g, 0.34 mmol), dry ammonium acetate (0.26 g, 3.40 mmol), 2c (0.11 g, 0.34 mmol) and dry methanol (2.0 mL) at 100 °C for 12 h to yield 72 mg (63.4%) of 4-(Pyridin-2-yl)-2-(pyridin-4-yl)-5,6-dihydro-1,10-phenanthroline (12) as a white solid.	null	6a, 2c	4-(Pyridin-2-yl)-2-(pyridin-4-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	63.4	isolated	success	100 °C	12 h	72 mg isolated	null	c1ccc(-c2cc(-c3ccncc3)nc3c2CCc2cccnc2-3)nc1
22,000,119	22000119	Reacting 7c (0.07 g, 0.30 mmol), dry ammonium acetate (0.23 g, 3.00 mmol), 2a (0.10 g, 0.30 mmol), and glacial acetic acid (0.5 mL) at 100 °C for 12 h yielded 37 mg (0.11 mmol, 36.1%) of 2-(Pyridin-2-yl)-4-(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline (34) as a light yellow solid.	null	7c, 2a	2-(Pyridin-2-yl)-4-(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate	null	glacial acetic acid	36.1	isolated	success	100 °C	12 h	37 mg isolated	null	c1ccc(-c2cc(-c3ccncc3)c3c(n2)-c2ccsc2CC3)nc1
22,000,119	22000119	The procedure described at Section 4.4 was employed with 6a (0.09 g, 0.40 mmol), dry ammonium acetate (0.31 g, 4.00 mmol), 2d (0.13 g, 0.40 mmol), and dry methanol (2.5 mL) at 100 °C for 12 h to yield 124 mg (0.37 mmol, 92.4%) of 13 as a white solid.	null	6a, 2d	2-Phenyl-4-(pyridin-2-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	92.4	isolated	success	100 °C	12 h	124 mg of product obtained as a white solid	null	c1ccc(-c2cc(-c3ccccn3)c3c(n2)-c2ncccc2CC3)cc1
22,000,119	22000119	Compound 23 (4-Phenyl-2-(pyridin-3-yl)-5,6-dihydro-1,10-phenanthroline) was synthesized by reacting 6d (0.09 g, 0.40 mmol), dry ammonium acetate (0.30 g, 4.00 mmol), and 2b (0.13 g, 0.40 mmol) in dry methanol (2.5 mL) at 100 °C for 16 h, yielding 81 mg (60.3%) of the product as a white solid.	null	6d, 2b	4-Phenyl-2-(pyridin-3-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	60.3	isolated	success	100 °C	16 h	0.09 g 6d, 0.30 g ammonium acetate, 0.13 g 2b, 2.5 mL dry methanol	null	c1ccc(-c2cc(-c3cccnc3)nc3c2CCc2cccnc2-3)cc1
34,418,288	34418288	For the preparation of the catalyst (6), 1-methylimidazole and 3-trimethoxysilylpropyl chloride compounds were mixed and refluxed for 48 h to generate 1-methyl-3-(3-trimethoxysilylpropyl) imidazolium chloride.	alkylation	1-methylimidazole, 3-trimethoxysilylpropyl chloride	1-methyl-3-(3-trimethoxysilylpropyl) imidazolium chloride	null	null	null	null	null	success	reflux	48 h	null	null	CO[Si](CCC[n+]1ccn(C)c1)(OC)OC.[Cl-]
22,000,119	22000119	Compound 24 (4-Phenyl-2-(pyridin-4-yl)-5,6-dihydro-1,10-phenanthroline) was synthesized using 6d (0.07 g, 0.30 mmol), dry ammonium acetate (0.23 g, 3.00 mmol), and 2c (0.10 g, 0.30 mmol) in dry methanol (2.5 mL) at 100 °C for 16 h, yielding 26 mg (26.2%) of the product as a white solid.	null	6d, 2c	4-Phenyl-2-(pyridin-4-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	26.2	isolated	success	100 °C	16 h	26 mg isolated; dry ammonium acetate and dry methanol used	null	c1ccc(-c2cc(-c3ccncc3)nc3c2CCc2cccnc2-3)cc1
22,000,119	22000119	The procedure described at Section 4.5 was employed with 7c (0.07 g, 0.30 mmol), dry ammonium acetate (0.23 g, 3.00 mmol), 2c (0.10 g, 0.30 mmol), and glacial acetic acid (0.5 mL) at 100 °C for 16 h to yield 28 mg (0.08 mmol, 27.6%) of 2,4-Di(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline (36) as an off-white solid.	null	7c, 2c	2,4-Di(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate, glacial acetic acid	null	glacial acetic acid	27.6	isolated	success	100 °C	16 h	28 mg isolated; off-white solid	null	c1cc(-c2cc(-c3ccncc3)c3c(n2)-c2ccsc2CC3)ccn1
22,000,119	22000119	The reaction of 7a (0.10 g, 0.41 mmol), dry ammonium acetate (0.32 g, 4.10 mmol), 2a (0.13 g, 0.41 mmol), and glacial acetic acid (1.5 mL) at 100 °C for 20 h yielded 43 mg (0.12 mmol, 31.0%) of 2,4-Di(pyridin-2-yl)-5,6-dihydrothieno[2,3-h]quinoline (26) as an off-white solid.	null	7a, 2a	2,4-Di(pyridin-2-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate, glacial acetic acid	null	glacial acetic acid	31	isolated	success	100 °C	20 h	43 mg isolated	null	c1ccc(-c2cc(-c3ccccn3)c3c(n2)-c2ccsc2CC3)nc1
22,000,119	22000119	Using the procedure described at Section 4.5, 7d (0.09 g, 0.37 mmol), dry ammonium acetate (0.28 g, 3.70 mmol), 2b (0.12 g, 0.37 mmol), and glacial acetic acid (1 mL) were reacted at 100 °C for 20 h to yield 30 mg (24.2%) of 4-Phenyl-2-(pyridin-3-yl)-5,6-dihydrothieno[2,3-h]quinoline (39) as a light yellow solid.	null	7d, 2b	4-Phenyl-2-(pyridin-3-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate	null	glacial acetic acid	24.2	isolated	success	100 °C	20 h	30 mg isolated; light yellow solid	null	c1ccc(-c2cc(-c3cccnc3)nc3c2CCc2sccc2-3)cc1
22,000,119	22000119	The procedure described at Section 4.4 was employed with 6a (0.10 g, 0.42 mmol), dry ammonium acetate (0.32 g, 4.20 mmol), 2a (0.13 g, 0.42 mmol), and dry methanol (2.5 mL) at 100 °C for 12 h to yield 60 mg (0.19 mmol, 42.6%) of 2,4-Di(pyridin-2-yl)-5,6-dihydro-1,10-phenanthroline (10) as a light yellow solid.	null	6a, 2a	2,4-Di(pyridin-2-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	42.6	isolated	success	100 °C	12 h	60 mg isolated	null	c1ccc(-c2cc(-c3ccccn3)c3c(n2)-c2ncccc2CC3)nc1
22,000,119	22000119	Using the procedure from Section 4.5, 7b (0.15 g, 0.62 mmol), dry ammonium acetate (0.48 g, 6.20 mmol), 2b (0.30 g, 0.93 mmol), and dry methanol (5 mL) were reacted at 100 °C for 24 h to yield 25 mg (12.0%) of 2,4-Di(pyridin-3-yl)-5,6-dihydrothieno[2,3-h]quinoline (31) as a white solid.	null	7b, 2b	2,4-Di(pyridin-3-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate	null	methanol	12	isolated	success	100 °C	24 h	25 mg isolated; dry ammonium acetate and dry methanol used	null	c1cncc(-c2cc(-c3cccnc3)c3c(n2)-c2ccsc2CC3)c1
16,011,324	16011324	Alkylation of the dihydroisoquinoline 235 with trimethylsilylmethyl triflate gave the intermediate iminium salt 236, which was treated with cesium fluoride to give the cycloadduct 237 (Scheme 63).	alkylation	compound 235, trimethylsilylmethyl triflate	compound 236	null	null	null	null	null	success	null	null	null	null	C1=Cc2ccccc2CN1
16,011,324	16011324	Alkylation of the substituted 3,4-dihydroisoquinoline 244 with the iodide 245 gave the salt 246, which was not isolated but treated immediately with base and heated in 1,2-dichloroethane... to give lamellarin K triisopropyl ether 247.	alkylation	substituted 3,4-dihydroisoquinoline 244, iodide 245	compound 246	null	null	null	null	null	success	null	null	Salt 246 was not isolated.	null	C1=NCCc2ccccc21
22,000,119	22000119	A procedure described at Section 4.4 was used with 6d (0.09 g, 0.40 mmol), dry ammonium acetate (0.30 g, 4.00 mmol), 2a (0.13 g, 0.40 mmol), and dry methanol (2.5 mL) at 100 °C for 16 h to yield 88 mg (65.6%) of 4-Phenyl-2-(pyridin-2-yl)-5,6-dihydro-1,10-phenanthroline (22) as a white solid.	null	6d, 2a	4-Phenyl-2-(pyridin-2-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	65.6	isolated	success	100 °C	16 h	88 mg (0.26 mmol) isolated as a white solid; dry methanol used	null	c1ccc(-c2cc(-c3ccccn3)nc3c2CCc2cccnc2-3)cc1
27,960,274	27960274	The asymmetric vinylogous Mannich reaction of aromatic, heteroaromatic, and aliphatic N-aryl aldimines 37a–37h with N-Boc-2-(trimethylsiloxy)pyrrole 32 afforded chiral α,β-unsaturated δ-amino-γ-butyrolactams 38a–38h with yields of 36–99%.	vinylogous Mannich reaction	N-aryl aldimines 37a–37h, N-Boc-2-(trimethylsiloxy)pyrrole 32	chiral α,β-unsaturated δ-amino-γ-butyrolactams 38a–38h	null	null	null	null	unspecified	success	null	null	Yields ranged from 36-99%.	null	CC(C)(C)OC(=O)n1cccc1O[Si](C)(C)C
27,960,274	27960274	A three-component Mannich reaction between alkyl-substituted aldehydes 5a–5g, o-thiomethyl-p-anisidine 17, and N-Boc-2-(trimethylsiloxy)pyrrole 32 using a catalyst system at 5 mol % loading afforded vicinal chiral diamino carbonyl products 39a–39g in yields of 51–92%.	Mannich reaction	alkyl-substituted aldehydes 5a–5g, o-thiomethyl-p-anisidine 17, N-Boc-2-(trimethylsiloxy)pyrrole 32	vicinal chiral diamino carbonyl products 39a–39g	null	null	null	null	unspecified	success	null	null	5 mol % catalyst loading; yields ranged from 51-92%.	null	CC(C)(C)OC(=O)n1cccc1O[Si](C)(C)C
27,960,274	27960274	Hoveyda reinvestigated the three-component Mannich reaction of cyclohexylcarboxaldehyde (R = Cy) with o-thiomethyl-p-anisidine and N-Boc-2-(trimethylsiloxy)pyrrole in the presence of 5 mol % of iso-leucine-derived phosphine ligand 27 and 5 mol % of AgOAc, which led to the corresponding Mannich product in 82% yield.	Mannich reaction	cyclohexylcarboxaldehyde, o-thiomethyl-p-anisidine, N-Boc-2-(trimethylsiloxy)pyrrole	Mannich product	AgOAc	iso-leucine-derived phosphine ligand 27	null	82	unspecified	success	null	null	5 mol % ligand 27 and 5 mol % AgOAc.	null	O=CC1CCCCC1
27,960,274	27960274	Shi et al. used chiral phosphine Schiff base type ligands (11 mol %) and AgOAc (10 mol %) to promote the enantioselective Mannich reaction of aromatic N-aryl aldimines 40a–40h with trimethylsiloxyfuran 18a, producing chiral Mannich products 42a–42h with yields of 51–91%.	Mannich reaction	aromatic N-aryl aldimines 40a–40h, trimethylsiloxyfuran 18a	chiral Mannich products 42a–42h	AgOAc	chiral phosphine Schiff base type ligands	null	null	unspecified	success	null	null	11 mol % ligand and 10 mol % AgOAc; yields ranged from 51-91%.	null	C[Si](C)(C)Oc1ccco1
27,960,274	27960274	It was found that the use of benzyl alcohol as superstoichiometric additive was important to achieve better yield and diastereoselectivity as well as enantioselectivity in the reaction of aromatic N-aryl aldimines 40a–40h with trimethylsiloxyfuran 18a using ligand 41 and AgOAc.	Mannich reaction	aromatic N-aryl aldimines 40a–40h, trimethylsiloxyfuran 18a	chiral Mannich products 42a–42h	AgOAc, benzyl alcohol	ligand 41	null	null	unspecified	success	null	null	Benzyl alcohol used as superstoichiometric additive.	null	C[Si](C)(C)Oc1ccco1
22,000,119	22000119	Compound 16, 4-(Pyridin-3-yl)-2-(pyridin-4-yl)-5,6-dihydro-1,10-phenanthroline, was synthesized using 6b (0.12 g, 0.50 mmol), dry ammonium acetate (0.38 g, 5.00 mmol), 2c (0.16 g, 0.50 mmol), and dry methanol (2.5 mL) at 100 °C for 12 h to yield 58 mg (34.5%) as a white solid.	null	6b, 2c	4-(Pyridin-3-yl)-2-(pyridin-4-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	34.5	isolated	success	100 °C	12 h	58 mg isolated; 0.12 g of 6b, 0.38 g of ammonium acetate, 0.16 g of 2c, 2.5 mL of methanol	null	c1cncc(-c2cc(-c3ccncc3)nc3c2CCc2cccnc2-3)c1
24,090,404	24090404	N-(1-(2,6-Dibutylphenyl)ethyl)picolinamide was synthesized by charging a 2-dram screw-cap vial with Pd(OAc)₂ (10 mol%), CuBr₂ (20 mol %), N-(1-phenylethyl)picolinamide (1 mmol), n-butyl iodide (4 mmol), K₂CO₃ (4 mmol), and water (0.30 mL), then stirring at 120 °C for 24 h.	alkylation	N-(1-phenylethyl)picolinamide, n-butyl iodide	N-(1-(2,6-Dibutylphenyl)ethyl)picolinamide	K₂CO₃	Pd(OAc)₂, CuBr₂	water	99	isolated	success	120 °C	24 h	2-dram screw-cap vial	null	CCCCc1cccc(CCCC)c1C(C)NC(=O)c1ccccn1
22,000,119	22000119	The procedure described at Section 4.5 was employed with 7b (0.07 g, 0.29 mmol), dry ammonium acetate (0.22 g, 2.90 mmol), 2c (0.09 g, 0.29 mmol), and glacial acetic acid (0.5 mL) at 90 °C for 14 h to yield 32 mg (0.09 mmol, 31.7%) of 4-(Pyridin-3-yl)-2-(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline (32) as a light y...	null	7b, 2c	4-(Pyridin-3-yl)-2-(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate, glacial acetic acid	null	glacial acetic acid	31.7	isolated	success	90 °C	14 h	32 mg of product isolated	null	c1cncc(-c2cc(-c3ccncc3)nc3c2CCc2sccc2-3)c1
10,814,067	10814067	The general procedure using workup method B gave 211 mg (94%) of N-(4-Acetylphenyl)-m-toluidine as a yellow solid.	null	null	N-(4-Acetylphenyl)-m-toluidine	null	null	null	94	isolated	success	null	null	211 mg isolated; used workup method B; prepared via general procedure	null	CC(=O)c1ccc(Nc2cccc(C)c2)cc1
32,637,839	32637839	Diethyl aminomalonate hydrochloride S1 (3.62 g, 17.1 mmol) was reacted with benzophenoneimine (3.13 g, 17.1 mmol) in dichloromethane (60 mL) at room temperature for 24 h to give 2-aminomalonate 5a (4.67 g, 80%).	condensation	diethyl aminomalonate hydrochloride, benzophenoneimine	2-aminomalonate 5a	null	null	dichloromethane	80	isolated	success	room temperature	24 h	Argon atmosphere; purified by column chromatography on silica gel (hexane/EtOAc = 10:1).	null	NC(C(=O)[O-])C(=O)[O-]
32,637,839	32637839	Crude 2-aminomalonate (prepared from diethyl aminomalonate hydrochloride S1 and saturated aqueous NaHCO3) was reacted with (MeO)2CNMe2 (4.64 mg, 39.0 mmol) in toluene (60 mL) under reflux for 30 min and then at room temperature for 12 h to give diethyl 2-aminomalonate 5b (6.23 g, 90%).	condensation	2-aminomalonate, (MeO)2CNMe2	diethyl 2-aminomalonate 5b	null	null	toluene	90	isolated	success	reflux	12.5 h	Argon atmosphere; reaction stirred under reflux for 30 min and then at room temperature for 12 h.	null	CCOC(=O)C(/N=C/N(C)C)C(=O)OCC
32,637,839	32637839	Substrates 3, which are 3-amino-4-(2-bromophenyl)-2-pyridones, could be obtained by the conjugate addition of diethyl 2-aminomalonate 5 to alkynyl imines 4 with a bromo group.	conjugate addition	diethyl 2-aminomalonate, alkynyl imines 4	3-amino-4-(2-bromophenyl)-2-pyridones 3	null	null	null	null	null	success	null	null	null	null	Nc1ccc[nH]c1=O
32,637,839	32637839	2,3-disubstituted 4-ethoxycarbonyl-β-carbolin-1-ones 1 could be obtained by the intramolecular amination of 3-amino-4-(2-bromophenyl)-2-pyridones 2.	intramolecular amination	3-amino-4-(2-bromophenyl)-2-pyridones 2	2,3-disubstituted 4-ethoxycarbonyl-β-carbolin-1-ones 1	null	palladium	null	null	null	success	null	null	The synthesis uses palladium-catalyzed intramolecular amination as described in the abstract.	null	O=C1N=CC=C2C1=Nc1ccccc12
31,626,546	31626546	Hydroxycarbonimidic dibromide (4, 8.15 g, 40.2 mmol) was dissolved in CH₂Cl₂ (100 mL), and 2-bromo-3,3,3-trifluoro-1-propene (2, 21.1 g, 121 mmol) and NaHCO₃ (11.1 g, 133 mmol) were added to the vigorously stirred homogeneous solution at rt. The resulting mixture was stirred overnight, yielding 3,5-Dibromo-5-(trifluoro...	cycloaddition	hydroxycarbonimidic dibromide, 2-bromo-3,3,3-trifluoro-1-propene	3,5-Dibromo-5-(trifluoromethyl)-4,5-dihydroisoxazole	NaHCO₃	null	CH₂Cl₂	63	isolated	success	rt	overnight	vigorously stirred homogeneous solution; purified by distillation in vacuo	null	FC(F)(F)C1(Br)CC(Br)=NO1
22,000,119	22000119	The procedure described at Section 4.4 was employed using 6c (0.08 g, 0.35 mmol), dry ammonium acetate (0.27 g, 3.50 mmol), 2c (0.11 g, 0.35 mmol), and dry methanol (2.5 mL) at 95 °C for 14 h to yield 66 mg (56.1%) of 2,4-Di(pyridin-4-yl)-5,6-dihydro-1,10-phenanthroline (20) as a white solid.	null	6c, 2c	2,4-Di(pyridin-4-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	56.1	isolated	success	95 °C	14 h	66 mg isolated; dry ammonium acetate and dry methanol used.	null	c1cnc2c(c1)CCc1c(-c3ccncc3)cc(-c3ccncc3)nc1-2
22,000,119	22000119	A procedure was employed using 7a (0.14 g, 0.60 mmol), dry ammonium acetate (0.46 g, 6.00 mmol), 2c (0.19 g, 0.60 mmol), and glacial acetic acid (1.0 mL) at 100 °C for 20 h to yield 87 mg (42.5%) of 4-(Pyridin-2-yl)-2-(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline (28) as a light yellow solid.	null	7a, 2c	4-(Pyridin-2-yl)-2-(pyridin-4-yl)-5,6-dihydrothieno[2,3-h]quinoline	ammonium acetate	null	glacial acetic acid	42.5	isolated	success	100 °C	20 h	87 mg isolated	null	c1ccc(-c2cc(-c3ccncc3)nc3c2CCc2sccc2-3)nc1
32,637,839	32637839	Nitrone S3f(28), CuI, DPPE, and K2CO3 in DMF and H2O were reacted with 1-bromo-2-ethynylbenzene S2a at 80 °C for 4 h to give alkynyl imine 4f (834 mg, 70%).	coupling	nitrone S3f(28), 1-bromo-2-ethynylbenzene S2a	(Z)-3-(2-Bromophenyl)-N-(4-chlorophenyl)-1-phenylprop-2-yn-1-imine (4f)	K2CO3, DPPE	CuI	DMF, H2O	70	isolated	success	80 °C	4 h	Reaction performed in a 30 mL two-neck round-bottom flask under an argon balloon.	null	Clc1ccc(/N=C(\C#Cc2ccccc2Br)c2ccccc2)cc1
32,637,839	32637839	Aldehyde S5g and nitroarene S4g were stirred in H2O, EtOH, and NH4Cl at room temperature for 15 min, followed by the addition of Zn powder at 0 °C and stirring at room temperature for 15 h to give nitrone S3g (870 mg, 41%).	nitrone synthesis	aldehyde S5g, nitroarene S4g	(Z)-N-Phenyl-1-(p-tolyl)methanimine Oxide (S3g)	NH4Cl, Zn powder	null	H2O, EtOH	41	isolated	success	rt	15 h	Reaction performed in a 300 mL two-neck round-bottom flask under an argon balloon; Zn powder added at 0 °C.	null	Cc1ccc(/C=[N+](\[O-])c2ccccc2)cc1
22,000,119	22000119	The procedure described at Section 4.4 was employed with 6b (0.07 g, 0.30 mmol), dry ammonium acetate (0.23 g, 3.00 mmol), 2b (0.10 g, 0.30 mmol), and dry methanol (2.0 mL) at 100 °C for 12 h to yield 58 mg (0.17 mmol, 57.5%) of 2,4-Di(Pyridin-3-yl)-5,6-dihydro-1,10-phenanthroline (15) as a white solid.	null	6b, 2b	2,4-Di(Pyridin-3-yl)-5,6-dihydro-1,10-phenanthroline	ammonium acetate	null	methanol	57.5	isolated	success	100 °C	12 h	58 mg isolated; white solid	null	c1cncc(-c2cc(-c3cccnc3)c3c(n2)-c2ncccc2CC3)c1
11,848,747	11848747	The (Z)-propenyl ether (Z)-V reacts to give a quaternary mixture of nitroso acetals in 83% yield.	cycloaddition	(Z)-V	nitroso acetals	null	null	null	83	unspecified	success	null	null	null	The product is described as a quaternary mixture.	C/C=C\O/C=C\C
11,848,747	11848747	With MAPh as the Lewis acid, the lactams formed after hydrogenation are now enriched in the exo diastereomer a.	cycloaddition	(Z)-VI	lactams	null	MAPh	null	null	unspecified	success	null	null	Lactams formed after hydrogenation.	The reaction produces an enrichment in the exo diastereomer a.	[CH3][Al]([O]c1c(-c2ccccc2)cccc1-c1ccccc1)[O]c1c(-c2ccccc2)cccc1-c1ccccc1
11,848,747	11848747	The full evaluation of 2,2-diphenylcyclopentanol as an auxiliary is seen in the examination of (E)-propenyl ether (E)-VI in the test cycloaddition with both Lewis acids... With MAPh as the promoter, the nitroso acetals are formed in 83% yield.	cycloaddition	(E)-VI	nitroso acetals	null	MAPh	null	83	unspecified	success	null	null	Product formed as a mixture of two diastereomers in a ratio of 7/1.	null	[CH3][Al]([O]c1c(-c2ccccc2)cccc1-c1ccccc1)[O]c1c(-c2ccccc2)cccc1-c1ccccc1
32,637,839	32637839	3-amino-2-pyridone 2a (48.9 mg, 0.100 mmol) in degassed 1,4-dioxane (2 mL) was reacted with Pd2(dba)3 (2.3 mg, 0.0025 mmol), SPhos (3.1 mg, 0.0075 mmol), and NaOtBu (19.2 mg, 0.200 mmol) under reflux for 4 h to give β-carbolin-1-one 1a (33.1 mg, 83%).	intramolecular amination	3-amino-2-pyridone 2a	Ethyl 1-Oxo-2,3-diphenyl-2,9-dihydro-1H-pyrido[3,4-b]indole-4-carboxylate	NaOtBu, SPhos	Pd2(dba)3	1,4-dioxane	83	isolated	success	reflux	4 h	argon balloon, degassed solvent	null	CCOC(=O)c1c(-c2ccccc2)n(-c2ccccc2)c(=O)c2[nH]c3ccccc3c12

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Chemical Reaction Extraction Task

Starling query: Find all reactions within PubMed.

Schema Specification

`reaction_type`

Type: string
Description: Type of reaction (e.g., Suzuki coupling, hydrogenation, oxidation, reduction, alkylation, acylation, condensation, cycloaddition)

`reactants`

Type: string
Description: All reactants/substrates whose atoms end up in the product, comma-separated. Do NOT include reagents, bases, catalysts, or solvents.

`product`

Type: string
Description: Primary product, name as written in the paper.

`reagent`

Type: string
Description: Bases, stoichiometric reagents, ligands, and additives — comma-separated (e.g., 'K2CO3, XPhos, TBAI'). Not catalysts or solvents. Null if none.

`catalyst`

Type: string
Description: Catalyst or catalytic system (e.g., 'Pd(PPh3)4', '10% Pd/C', 'Grubbs II', 'CuI', 'PPTS', 'TiCl4'). Include Lewis acids, phase-transfer catalysts, and organocatalysts. Only exclude stoichiometric reagents like NaBH4 or bases like K2CO3 (those go in reagent). Null if no catalyst.

`solvent`

Type: string
Description: Reaction solvent(s), comma-separated. Not workup solvents. Null if not reported.

`yield_percent`

Type: number
Description: Yield in percent (0 for failed reactions). Null only if not reported at all.

`yield_type`

Type: string
Description: How yield was measured.
Allowed values:
- isolated
- GC
- NMR
- LCMS
- HPLC
- crude
- quantitative
- unspecified

`outcome_status`

Type: string
Description: Reaction outcome.
Allowed values:
- success
- failed
- trace
- no_reaction
- decomposition

`temperature`

Type: string
Description: Reaction temperature with units (e.g., '80 °C', 'reflux', 'rt', '-78 °C'). If multiple stages, list the main reaction temperature. Null if not reported.

`reaction_time`

Type: string
Description: Reaction duration (e.g., '2 h', '30 min', 'overnight'). Null if not reported.

`setup_and_notes`

Type: string
Description: Atmosphere (N2, Ar, air), pressure, scale, concentration, equivalents, vessel, and any other relevant conditions not captured above. Null if nothing to add.

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Starling Artifacts

Collection

These are the artifacts associated with the initial release of the Starling Agent. • 7 items • Updated Jul 22