二苯二硫醚和可见光促进NHC-硼烷对亚胺的反硼氢化反应。
Inverse Hydroboration of Imines with NHC-Boranes Is Promoted by Diphenyl Disulfide and Visible Light.
作者信息
Kawamoto Takuji, Morioka Tsubasa, Noguchi Kohki, Curran Dennis P, Kamimura Akio
机构信息
Department of Applied Chemistry, Yamaguchi University, Ube, Yamaguchi 755-8611, Japan.
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
出版信息
Org Lett. 2021 Mar 5;23(5):1825-1828. doi: 10.1021/acs.orglett.1c00230. Epub 2021 Feb 23.
We describe a simple and efficient procedure for nucleophilic borylation of imines in the absence of a photoredox catalyst. Visible light irradiation of an acetonitrile solution of an imine, an NHC-borane, and diphenyl disulfide (10 mol %) provides various stable α-amino NHC-boranes in good yields. The reaction proceeds via addition of a nucleophilic boryl radical to an imine, followed by hydrogen abstraction from thiophenol, which is generated from NHC-borane and diphenyl disulfide.
我们描述了一种在无光氧化还原催化剂存在下对亚胺进行亲核硼化的简单有效方法。对亚胺、N-杂环卡宾硼烷和二苯基二硫化物（10 mol%）的乙腈溶液进行可见光照射，可高产率地得到各种稳定的α-氨基N-杂环卡宾硼烷。该反应通过亲核硼自由基加成到亚胺上，然后从N-杂环卡宾硼烷和二苯基二硫化物生成的苯硫酚中夺取氢来进行。
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