An Enantioselective Bidentate Auxiliary Directed Palladium‐Catalyzed Benzylic C−H Arylation of Amines Using a BINOL Phosphate Ligand | Zendy

Wang Hao | Zendy; Tong HuaRong | Zendy; He Gang | Zendy; Chen Gong | Zendy

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An Enantioselective Bidentate Auxiliary Directed Palladium‐Catalyzed Benzylic C−H Arylation of Amines Using a BINOL Phosphate Ligand

Author(s) -

Wang Hao,

Tong HuaRong,

He Gang,

Chen Gong

Publication year - 2016

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201609337

Subject(s) - enantioselective synthesis , chemistry , palladium , ligand (biochemistry) , denticity , phosphoric acid , catalysis , medicinal chemistry , alkyl , solvent , combinatorial chemistry , stereochemistry , organic chemistry , receptor , crystal structure , biochemistry

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, Cs 2 CO 3 , 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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