TY - JOUR
T1 - An Enantioselective Bidentate Auxiliary Directed Palladium-Catalyzed Benzylic C−H Arylation of Amines Using a BINOL Phosphate Ligand
AU - Wang, Hao
AU - Tong, Hua Rong
AU - He, Gang
AU - Chen, Gong
N1 - Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2016/12/5
Y1 - 2016/12/5
N2 - A new enantioselective palladium(II)-catalyzed benzylic C−H arylation reaction of amines is enabled by the bidentate picolinamide (PA) directing group. This reaction provides the first example of enantioselective benzylic γ-C−H arylations of alkyl amines, and proceeds with up to 97 % ee. The 2,2′-dihydroxy-1,1′-binaphthyl (BINOL) phosphoric acid ligand, Cs2CO3, and solvent-free conditions are essential for high enantioselectivity. Mechanistic studies suggest that multiple BINOL ligands are involved in the stereodetermining C−H palladation step.
AB - A new enantioselective palladium(II)-catalyzed benzylic C−H arylation reaction of amines is enabled by the bidentate picolinamide (PA) directing group. This reaction provides the first example of enantioselective benzylic γ-C−H arylations of alkyl amines, and proceeds with up to 97 % ee. The 2,2′-dihydroxy-1,1′-binaphthyl (BINOL) phosphoric acid ligand, Cs2CO3, and solvent-free conditions are essential for high enantioselectivity. Mechanistic studies suggest that multiple BINOL ligands are involved in the stereodetermining C−H palladation step.
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U2 - 10.1002/anie.201609337
DO - 10.1002/anie.201609337
M3 - Article
C2 - 27862771
AN - SCOPUS:85027931364
SN - 1433-7851
VL - 55
SP - 15387
EP - 15391
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 49
ER -