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苯并[3,4]环癸-3-烯-1,5-二炔与氮杂环卡宾硼烷的硼氢化自由基环化反应

Borylative Radical Cyclizations of Benzo[3,4]cyclodec-3-ene-1,5-diynes and N-Heterocyclic Carbene-Boranes.

作者信息

Watanabe Takashi, Hirose Daisuke, Curran Dennis P, Taniguchi Tsuyoshi

机构信息

School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.

Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.

出版信息

Chemistry. 2017 Apr 24;23(23):5404-5409. doi: 10.1002/chem.201700689. Epub 2017 Mar 27.

Abstract

Borylative radical cyclization of benzo[3,4]cyclodec-3-ene-1,5-diynes to provide 5-borylated 6,7,8,9-tetrahydrobenzo[a]azulenes has been developed. The experimental results suggest that the reaction proceeds by a radical chain mechanism, in which di-tert-butyl hyponitrite (TBHN) works as a good radical initiator to form boryl radicals from N-heterocyclic carbene-boranes (NHC-boranes). The present reaction is a rare model that illustrates addition of boryl radicals to alkynes.

摘要

已开发出苯并[3,4]环癸-3-烯-1,5-二炔的硼化自由基环化反应,以提供5-硼化的6,7,8,9-四氢苯并[a]薁。实验结果表明,该反应通过自由基链机制进行,其中二叔丁基亚硝酸盐(TBHN)作为良好的自由基引发剂,从氮杂环卡宾硼烷(NHC-硼烷)形成硼自由基。本反应是一个罕见的模型,说明了硼自由基与炔烃的加成反应。

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