Metal, iodine and oxidant-free electrosynthesis of substituted indoles from 1-(2-aminophenyl)alcohols

Chengcheng Yuan; Xiangxing Huang; Yi Lu; Zheng Fang; Chengkou Liu; Beining Chen; Kai Guo

doi:10.1016/j.gresc.2022.12.002

Metal, iodine and oxidant-free electrosynthesis of substituted indoles from 1-(2-aminophenyl)alcohols

Chengcheng Yuan, Xiangxing Huang, Yi Lu, Zheng Fang, Chengkou Liu, Beining Chen, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

A green and straightforward electrosynthesis of substituted indoles has been developed through dehydration and intramolecular dehydrogenative C–N bond-forming radical cross-coupling from 1-(2-aminophenyl)alcohols under metal, iodine and oxidant-free conditions. This electrochemical indole synthesis strategy has an excellent functional group, water and air tolerance. And, a possible cyclization process was proposed based on the radical-trapping, intermediate verification, cyclic voltammetry, EPR and control experiments.

Original language	English
Pages (from-to)	311-315
Number of pages	5
Journal	Green Synthesis and Catalysis
Volume	4
Issue number	4
DOIs	https://doi.org/10.1016/j.gresc.2022.12.002
State	Published - Nov 2023

Keywords

C–N coupling
Electrosynthesis
Indoles
Iodine and oxidant-free
Metal
N-centered radicals

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10.1016/j.gresc.2022.12.002

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title = "Metal, iodine and oxidant-free electrosynthesis of substituted indoles from 1-(2-aminophenyl)alcohols",

abstract = "A green and straightforward electrosynthesis of substituted indoles has been developed through dehydration and intramolecular dehydrogenative C–N bond-forming radical cross-coupling from 1-(2-aminophenyl)alcohols under metal, iodine and oxidant-free conditions. This electrochemical indole synthesis strategy has an excellent functional group, water and air tolerance. And, a possible cyclization process was proposed based on the radical-trapping, intermediate verification, cyclic voltammetry, EPR and control experiments.",

keywords = "C–N coupling, Electrosynthesis, Indoles, Iodine and oxidant-free, Metal, N-centered radicals",

author = "Chengcheng Yuan and Xiangxing Huang and Yi Lu and Zheng Fang and Chengkou Liu and Beining Chen and Kai Guo",

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doi = "10.1016/j.gresc.2022.12.002",

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T1 - Metal, iodine and oxidant-free electrosynthesis of substituted indoles from 1-(2-aminophenyl)alcohols

AU - Yuan, Chengcheng

AU - Huang, Xiangxing

AU - Lu, Yi

AU - Fang, Zheng

AU - Liu, Chengkou

AU - Chen, Beining

AU - Guo, Kai

PY - 2023/11

Y1 - 2023/11

N2 - A green and straightforward electrosynthesis of substituted indoles has been developed through dehydration and intramolecular dehydrogenative C–N bond-forming radical cross-coupling from 1-(2-aminophenyl)alcohols under metal, iodine and oxidant-free conditions. This electrochemical indole synthesis strategy has an excellent functional group, water and air tolerance. And, a possible cyclization process was proposed based on the radical-trapping, intermediate verification, cyclic voltammetry, EPR and control experiments.

AB - A green and straightforward electrosynthesis of substituted indoles has been developed through dehydration and intramolecular dehydrogenative C–N bond-forming radical cross-coupling from 1-(2-aminophenyl)alcohols under metal, iodine and oxidant-free conditions. This electrochemical indole synthesis strategy has an excellent functional group, water and air tolerance. And, a possible cyclization process was proposed based on the radical-trapping, intermediate verification, cyclic voltammetry, EPR and control experiments.

KW - C–N coupling

KW - Electrosynthesis

KW - Indoles

KW - Iodine and oxidant-free

KW - Metal

KW - N-centered radicals

UR - http://www.scopus.com/inward/record.url?scp=85145282520&partnerID=8YFLogxK

U2 - 10.1016/j.gresc.2022.12.002

DO - 10.1016/j.gresc.2022.12.002

M3 - 文章

AN - SCOPUS:85145282520

SN - 2666-5549

VL - 4

SP - 311

EP - 315

JO - Green Synthesis and Catalysis

JF - Green Synthesis and Catalysis

IS - 4

ER -

Metal, iodine and oxidant-free electrosynthesis of substituted indoles from 1-(2-aminophenyl)alcohols

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Keywords

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