Electrooxidation enables highly regioselective dearomative annulation of indole and benzofuran derivatives

作者:Liu, K (Liu, Kun)[ 1 ] ; Song, WX (Song, Wenxu)[ 1 ] ; Deng, YQ (Deng, Yuqi)[ 1 ] ; Yang, HY (Yang, Huiyue)[ 1 ] ; Song, CL (Song, Chunlan)[ 1 ] ; Abdelilah, T (Abdelilah, Takfaoui)[ 1 ] ; Wang, SC (Wang, Shengchun)[ 1 ] ; Cong, HJ (Cong, Hengjiang)[ 1 ] ; Tang, S (Tang, Shan)[ 1 ] ; Lei, AW (Lei, Aiwen)[ 1 ]

NATURE COMMUNICATIONS

卷: 11 期: 1

文献号: 3

DOI: 10.1038/s41467-019-13829-4

出版年: JAN 7 2020

文献类型:Article

摘要

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.

关键词

KeyWords Plus:COUPLING REACTIONS; STRATEGY; BENZOFUROINDOLINES; FUNCTIONALIZATION; PYRROLOINDOLINES; CONSTRUCTION; ALKALOIDS; PHENOLS; ALKENES; ACCESS

作者信息

通讯作者地址:

Wuhan University Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies, Wuhan 430072, Peoples R China.

通讯作者地址: Lei, AW (通讯作者)

Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies, Wuhan 430072, Peoples R China.

地址:

[ 1 ]‎ Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies, Wuhan 430072, Peoples R China

电子邮件地址:aiwenlei@whu.edu.cn