Inverse Hydroboration of Imines with NHC-Boranes Is Promoted by Diphenyl Disulfide and Visible Light
Inverse Hydroboration of Imines with NHC-Boranes Is Promoted by Diphenyl Disulfide and Visible Light
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DOI：
10.1021/acs.orglett.1c00230
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发表时间：
2021-02-23
期刊：
影响因子：
5.2
通讯作者：
Kamimura, Akio
中科院分区：
文献类型：
--
作者：
Kawamoto, Takuji;Morioka, Tsubasa;Kamimura, Akio
我们描述了一种在没有光氧化还原催化剂的情况下亚胺的亲核硼化反应的简单而有效的方法。在可见光照射下，亚胺、NHC-硼烷和二苯二硫醚(10mol%)的乙腈溶液以良好的产率提供了各种稳定的α-氨基NFIC-硼烷。该反应通过在亚胺上加成亲核的硼基，然后从由NHC-硼烷和二苯二硫化物生成的硫酚中提取氢来进行。
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 alpha-amino NFIC-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.