Synlett 2021; 32(17): 1772-1776
DOI: 10.1055/s-0040-1720391
letter

(NH4)2S2O8-Promoted Direct C–C Coupling of Indoles with Quinones/Hydroquinones without Catalyst

Yu Dong
a   College of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. of China
,
Ji-Xian Ye
a   College of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. of China
,
Qi-Qi Luo
a   College of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. of China
,
Ting Mei
a   College of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. of China
,
Ai Shen
a   College of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. of China
,
Peng Huang
a   College of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. of China
,
Jia Chen
a   College of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. of China
,
Xia Zhang
a   College of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. of China
,
Chun Xie
a   College of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu, 611130, P. R. of China
,
Zhi-Chuan Shi
b   Southwest Minzu University, Chengdu, 610041, P. R. of China
› Author Affiliations
We are grateful for the financial support from the Foundation of Chengdu Normal University Talent Introduction Research Funding (2021YJRC202020).


Abstract

An atom-economical and environmentally benign approach for the synthesis of 3-indolylquinones was achieved successfully via direct oxidative C–C coupling of quinones/hydroquinones with indoles using (NH4)2S2O8 in dichloroethane at 80 °C. The efficiency of this catalytic approach was established by a broad scope of substrates involving quinones and hydroquinones to give high yields (61–93%) of 3-indolylquinones. The present protocol is simple, practical, and show good functional group tolerance. In addition, the obtained 3-indolylnaphthoquinones were conducted to further transformation to synthesize 2-amino-3-indolylnaphthoquinone and polycyclic N-heterocycles, respectively.

Supporting Information



Publication History

Received: 03 June 2021

Accepted after revision: 19 July 2021

Article published online:
12 August 2021

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