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Electrooxidation enables highly regioselective dearomative annulation of indole and benzofuran derivatives.


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.

SUBMITTER: Liu K 

PROVIDER: S-EPMC6946675 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Electrooxidation enables highly regioselective dearomative annulation of indole and benzofuran derivatives.

Liu Kun K   Song Wenxu W   Deng Yuqi Y   Yang Huiyue H   Song Chunlan C   Abdelilah Takfaoui T   Wang Shengchun S   Cong Hengjiang H   Tang Shan S   Lei Aiwen A  

Nature communications 20200107 1


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,  ...[more]

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