Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors

Shichun Jiang, Wei Wang, Chengli Mou, Juan Zou, Zhichao Jin (), Gefei Hao () and Yonggui Robin Chi ()
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Shichun Jiang: Guizhou University
Wei Wang: Guizhou University
Chengli Mou: Guizhou University of Traditional Chinese Medicine
Juan Zou: Guizhou University of Traditional Chinese Medicine
Zhichao Jin: Guizhou University
Gefei Hao: Guizhou University
Yonggui Robin Chi: Guizhou University

Nature Communications, 2023, vol. 14, issue 1, 1-12

Abstract: Abstract The development of suitable electron donors is critical to single-electron-transfer (SET) processes. The use of heteroatom-centered anions as super-electron-donors (SEDs) for direct SET reactions has rarely been studied. Here we show that heteroatom anions can be applied as SEDs to initiate radical reactions for facile synthesis of 3-substituted benzofurans. Phosphines, thiols and anilines bearing different substitution patterns work well in this inter-molecular radical coupling reaction and the 3-functionalized benzofuran products bearing heteroatomic functionalities are given in moderate to excellent yields. The reaction mechanism is elucidated via control experiments and computational methods. The afforded products show promising applications in both organic synthesis and pesticide development.

Date: 2023
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DOI: 10.1038/s41467-023-43198-y

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