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硼烷与氮杂环卡宾的连接:用于自由基反应的有效氢原子供体。

Linking borane with N-heterocyclic carbenes: effective hydrogen-atom donors for radical reactions.

作者信息

Walton John C

机构信息

School of Chemistry, University of St. Andrews, St. Andrews, Fife, KY16 9ST, UK.

出版信息

Angew Chem Int Ed Engl. 2009;48(10):1726-8. doi: 10.1002/anie.200805362.

Abstract

Undue influence: N-heterocyclic carbenes (NHCs) were found to reduce the strength of the B-H bonds of borane by a surprisingly large amount upon the formation of NHC-BH(3) complexes. This property was exploited in the development of a suite of NHC-borane complexes for the reduction of xanthates in radical-mediated Barton-McCombie-type deoxygenation reactions (see scheme). AIBN = azobisisobutyronitrile, Bn = benzyl.

摘要

不当影响

发现N-杂环卡宾(NHCs)在形成NHC-BH(3)配合物时,能使硼烷的B-H键强度大幅降低,降幅惊人。这一特性被用于开发一系列NHC-硼烷配合物,用于在自由基介导的巴顿-麦康比型脱氧反应中还原黄原酸酯(见方案)。AIBN = 偶氮二异丁腈,Bn = 苄基。

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