Chemoselective Hydroheteroarylation of Alkenes via Photoredox-Neutral Proton- and BF 3 -Mediated Electron Transfer

Herein, we have developed a complementary entry to enable hydroheteroarylation of alkenes involving basically photoredox dearomatizative heterocyclic carbon radical formation through acid-coupled electron transfer followed by Giese addition. While protonic solvent and thiophenol additive enabled two...

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Bibliographic Details
Published in:Organic letters 2024-09, Vol.26 (36), p.7707-7712
Main Authors: Wan, Xiaoyuan, Huang, Huawen, Deng, Yujie, Yuan, Yuezhou, Deng, Guo-Jun
Format: Article
Language:English
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Summary:Herein, we have developed a complementary entry to enable hydroheteroarylation of alkenes involving basically photoredox dearomatizative heterocyclic carbon radical formation through acid-coupled electron transfer followed by Giese addition. While protonic solvent and thiophenol additive enabled two molecular hydroheteroarylations of alkenes, the nonproton environment with BF altered the chemoselectivity over cascade hydroheteroarylation of alkenes by radical addition of heteroaromatics with two molecular alkenes. This chemoselectivity can be mechanistically attributed to the dynamically favored hydrogen atom transfer via the cyclic transition state.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c02825