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

Yu Dong; Ji-Xian Ye; Qi-Qi Luo; Ting Mei; Ai Shen; Peng Huang; Jia Chen; Xia Zhang; Chun Xie; Zhi-Chuan Shi

doi:10.1055/s-0040-1720391

Synlett, Table of Contents

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 ∗

^aCollege 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

^aCollege 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

^aCollege 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

^aCollege 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

^aCollege 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

^aCollege 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

^aCollege 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

^aCollege 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

^aCollege 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

^bSouthwest Minzu University, Chengdu, 610041, P. R. of China

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Abstract

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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.

Key words

quinones/hydroquinones - indoles - C–C coupling - 3-indolylquinones - (NH₄)₂S₂O₈-promoted

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