Journal
ORGANIC LETTERS
Volume 23, Issue 5, Pages 1825-1828Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00230
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Funding
- JSPS [18K14222]
- Naito Foundation
- Yazaki Memorial Foundation for Science and Technology, YU project for formation of the core research center (Yamaguchi University)
- Yamaguchi University Foundation
- Grants-in-Aid for Scientific Research [18K14222] Funding Source: KAKEN
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A simple and efficient procedure for nucleophilic borylation of imines without the need for a photoredox catalyst has been developed, resulting in stable products in good yields.
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.
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