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

Hao Wang, Hua‐Rong Tong, Gang He, Gong Chen

doi:10.1002/anie.201609337

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

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Hao Wang

State Key Laboratory and Institute of Elemento-Organic Chemistry Collaborative Innovation, Center of Chemical Science and Engineering (Tianjin) Nankai University Tianjin 300071 China
Hua‐Rong Tong

State Key Laboratory and Institute of Elemento-Organic Chemistry Collaborative Innovation, Center of Chemical Science and Engineering (Tianjin) Nankai University Tianjin 300071 China
Gang He

State Key Laboratory and Institute of Elemento-Organic Chemistry Collaborative Innovation, Center of Chemical Science and Engineering (Tianjin) Nankai University Tianjin 300071 China
Gong Chen

State Key Laboratory and Institute of Elemento-Organic Chemistry Collaborative Innovation, Center of Chemical Science and Engineering (Tianjin) Nankai University Tianjin 300071 China

書誌事項

公開日: 2016-11-11

権利情報

http://onlinelibrary.wiley.com/termsAndConditions#vor

DOI

10.1002/anie.201609337

公開者: Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>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 % <jats:italic>ee</jats:italic>. The 2,2′‐dihydroxy‐1,1′‐binaphthyl (BINOL) phosphoric acid ligand, Cs<jats:sub>2</jats:sub>CO<jats:sub>3</jats:sub>, 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.</jats:p>