Transition-Metal-Free BF3-Mediated Regioselective Direct Alkylation and Arylation of Functionalized Pyridines Using Grignard or Organozinc Reagents
Transition-Metal-Free BF3-Mediated Regioselective Direct Alkylation and Arylation of Functionalized Pyridines Using Grignard or Organozinc Reagents
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DOI：
10.1021/ja401146v
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发表时间：
2013-04-02
影响因子：
15
通讯作者：
Knochel, Paul
中科院分区：
文献类型：
--
作者：
Chen, Quan;du Jourdin, Xavier Mollat;Knochel, Paul
各种吡啶与烷基和芳基的区域选择性交叉偶联可以通过BF3中心点OEt2将格氏试剂或有机锌试剂加成到含有不同取代基(氯、溴、氰基、乙烯基、苯基、甲氧基、硝基等)的吡啶上。然后是氯苯基催化的氧化芳构化。良好的区域选择性和广泛的官能团耐受性使该方法在制备多官能团吡啶化合物方面具有很强的通用性。在这些偶联反应中不需要过渡金属催化剂。
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.