Patent ID: 7247731
Filing Date: 2007-07-24
Classification: C07C,C07D,C07F

Abstract:
1. A method, comprising the step of: combining a compound represented by ArX, a compound represented by HN(R′)R″, a transition metal, a ligand, and a base, thereby forming a compound represented by ArN(R′)R″: wherein Ar is selected from the set consisting of optionally substituted monocyclic and polycyclic aromatic and heteroaromatic moieties; X is selected from the set consisting of Cl, and Br; R′ and R″ are selected, independently for each occurrence, from the set consisting of H, alkyl, heteroalkyl, aryl, heteroaryl, aralkyl, alkoxyl, amino, trialkylsilyl, and triarylsilyl; R′ and R″, taken together, may form an optionally substituted ring consisting of 3-10 backbone atoms inclusive; said ring optionally comprising one or more heteroatoms beyond the nitrogen to which R′ and R″ are bonded; R′ and/or R″ may be covalently linked to Ar such that the amination reaction is intramolecular; the transition metal is palladium; the ligand of the present invention is selected from the group consisting of structures 1-7 inclusive: wherein A and B independently represent fused rings selected from the group consisting of monocyclic or polycyclic cycloalkyls, cycloalkenyls, aryls, and heterocyclic rings, said rings having 4 to 8 backbone atoms; X and Y represent, independently for each occurrence, N, P, As, OR, or SR; R, R R A and B independently are unsubstituted or substituted with R R R m is independently for each occurrence an integer in the range 0 to 8 inclusive; and the ligand, when chiral, is mixture of enantiomers or a single enantiomer; wherein X and Y represent, independently for each occurrence, N, P, As, OR, or SR; R, R R m is independently for each occurrence an integer in the range 0 to 8 inclusive; and the ligand, when chiral, is mixture of enantiomers or a single enantiomer; wherein X and Y represent, independently for each occurrence, N, P, As, OR, or SR; R, R R the B and B′ rings of the binaphthyl core independently are unsubstituted or substituted with R R m is independently for each occurrence an integer in the range 0 to 8 inclusive; and the ligand, when chiral, is mixture of enantiomers or a single enantiomer; wherein R is selected, independently for each occurrence, from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, and —(CH the A and A′ rings of the biphenyl core independently are unsubstituted or substituted with R R R m is independently for each occurrence an integer in the range 0 to 8 inclusive; and the ligand, when chiral, is mixture of enantiomers or a single enantiomer; wherein R is selected, independently for each occurrence, from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, and —(CH the A, B, A′, and B′ rings of the binaphthyl core independently are unsubstituted or substituted with R R R m is independently for each occurrence an integer in the range 0 to 8 inclusive; and the ligand, when chiral, is mixture of enantiomers or a single enantiomer; wherein R is selected, independently for each occurrence, from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, and —(CH the A and A′ rings of the biphenyl core independently are unsubstituted or substituted with R R R m is independently for each occurrence an integer in the range 0 to 8 inclusive; and the ligand, when chiral, is mixture of enantiomers or a single enantiomer; wherein R is selected, independently for each occurrence, from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, and —(CH the A, B, A′, and B′ rings of the binaphthyl core independently are unsubstituted or substituted with R R R m is independently for each occurrence an integer in the range 0 to 8 inclusive; and the ligand, when chiral, is mixture of enantiomers or a single enantiomer; and the base is selected from the set consisting of carbonates, phosphates, fluorides, and alkoxides.