Transition-Metal-Free BF3-Mediated Regioselective Direct Alkylation and Arylation of Functionalized Pyridines Using Grignard or Organozinc Reagents

被引：142

作者：

Chen, Quan ^{[1
]}

du Jourdin, Xavier Mollat ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 13期

基金：

欧洲研究理事会;

关键词：

ZINC BENZYLIC ORGANOMETALLICS; NICKEL/LEWIS ACID CATALYSIS; FRUSTRATED LEWIS PAIRS; C-H ARYLATION; N-OXIDES; STEREOSELECTIVE-SYNTHESIS; HETEROAROMATIC BASES; POLYFUNCTIONAL ARYL; FACILE SYNTHESIS; MIXED COPPER;

D O I：

10.1021/ja401146v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A formal regioselective cross-coupling of various pyridines with alkyl and aryl groups can be achieved by a BF3 center dot OEt2-mediated addition of Grignard or organozinc reagents to pyridines bearing various substituents (chloro, bromo, cyano, vinyl, phenyl, carbethoxy, nitro, etc.) followed by an oxidative aromatization mediated by chloranil. Good regioselectivity and wide functional group tolerance make this method very versatile for the preparation of polyfunctional pyridines. No transition-metal catalyst is required in these coupling reactions.

引用

收藏

页码：4958 / 4961

页数：4

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