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

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An Enantioselective Bidentate Auxiliary Directed Palladium‐Catalyzed Benzylic C−H Arylation of Amines Using a BINOL Phosphate Ligand
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2016-11-11 , DOI: 10.1002/anie.201609337
Hao Wang ₁ , Hua-Rong Tong ₁ , Gang He ₁ , Gong Chen _{1,

2}

Affiliation

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.

中文翻译：

使用BINOL磷酸盐配体的胺的对映选择性二齿辅助定向钯催化苯甲酰化C-H胺化反应

二齿吡啶甲酰胺（PA）导向基团可实现新的对映选择性钯（II）催化的胺的苄基CH芳基化反应。该反应提供了烷基胺对映选择性苄基γ-C-H芳基化的第一个实例，并以高达97％的ee进行。2,2'-二羟基-1,1'-联萘（BINOL）磷酸配体Cs ₂ CO ₃和无溶剂条件对于高对映选择性至关重要。机理研究表明，多个BINOL配体参与立体确定CH palpalation步骤。

更新日期：2016-11-11

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