Bromide-Promoted Visible-Light-Induced Reductive Minisci Reaction with Aldehydes

Radical addition is a robust tool for bond formation. While ketyl radical reactivity of aldehydes by photoredox has been well-established, herein, we have now revealed a pathway for umpolung addition of aldehydes with or without external reductant. Hence, the reductive alkylations and challenging be...

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Bibliographic Details
Published in:ACS catalysis 2020-01, Vol.10 (1), p.154-159
Main Authors: Wang, Zhongzhen, Liu, Qiong, Ji, Xiaochen, Deng, Guo-Jun, Huang, Huawen
Format: Article
Language:English
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Summary:Radical addition is a robust tool for bond formation. While ketyl radical reactivity of aldehydes by photoredox has been well-established, herein, we have now revealed a pathway for umpolung addition of aldehydes with or without external reductant. Hence, the reductive alkylations and challenging benzylations of nitrogen heteroarenes (i.e., Minisci reactions) are enabled by the bromide-promoted visible light-mediated photocatalysis. The present protocol offers a mild, viable method for late-stage alkylations and transition-metal-free benzylations of biologically active nitrogen-heteroarene molecules. Mechanistic studies are indicative of a bromide-initiated acyl radical mechanism in the absence of external reductant.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.9b04411