Electrooxidation enables highly regioselective dearomative annulation of indole and benzofuran derivatives

Kun Liu, Wenxu Song, Yuqi Deng, Huiyue Yang, Chunlan Song, Takfaoui Abdelilah, Shengchun Wang, Hengjiang Cong, Shan Tang and Aiwen Lei ()
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Kun Liu: Wuhan University
Wenxu Song: Wuhan University
Yuqi Deng: Wuhan University
Huiyue Yang: Wuhan University
Chunlan Song: Wuhan University
Takfaoui Abdelilah: Wuhan University
Shengchun Wang: Wuhan University
Hengjiang Cong: Wuhan University
Shan Tang: Wuhan University
Aiwen Lei: Wuhan University

Nature Communications, 2020, vol. 11, issue 1, 1-11

Abstract: Abstract The dearomatization of arenes represents a powerful synthetic methodology to provide three-dimensional chemicals of high added value. Here we report a general and practical protocol for regioselective dearomative annulation of indole and benzofuran derivatives in an electrochemical way. Under undivided electrolytic conditions, a series of highly functionalized five to eight-membered heterocycle-2,3-fused indolines and dihydrobenzofurans, which are typically unattainable under thermal conditions, can be successfully accessed in high yield with excellent regio- and stereo-selectivity. This transformation can also tolerate a wide range of functional groups and achieve good efficiency in large-scale synthesis under oxidant-free conditions. In addition, cyclic voltammetry, electron paramagnetic resonance (EPR) and kinetic studies indicate that the dehydrogenative dearomatization annulations arise from the anodic oxidation of indole into indole radical cation, and this process is the rate-determining step.

Date: 2020
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DOI: 10.1038/s41467-019-13829-4

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