Electrochemical oxidative cyclization of activated alkynes with diselenides or disulfides: access to functionalized coumarins or quinolinones

Jiawei Hua; Zheng Fang; Jia Xu; Mixue Bian; ChengKou Liu; Wei He; Ning Zhu; Zhao Yang; Kai Guo

doi:10.1039/C9GC02131K

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Electrochemical oxidative cyclization of activated alkynes with diselenides or disulfides: access to functionalized coumarins or quinolinones†

Jiawei Hua,^a Zheng Fang,^a Jia Xu,^a Mixue Bian,^a ChengKou Liu,^a Wei He,^a Ning Zhu,^a Zhao Yang^b and Kai Guo

*^ac

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* Corresponding authors

^a College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, China
E-mail: guok@njtech.edu.cn
Fax: +862558139935
Tel: +86 2558139926

^b College of Engineering, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210003, China

^c State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, China

Abstract

A direct electrochemical oxidative cyclization of alkynoates and alkynamides with diselenides or disulfides for the synthesis of coumarins and quinolinones bearing a chalcogen functional group has been developed. This green and efficient approach was realized through a constant current electrolysis in an undivided cell under metal-free and oxidant-free conditions. Moreover, a series of selenium/sulfur-substituted coumarin and quinolinone products were obtained in moderate to good yields with a broad scope and functional group tolerance.

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DOI: https://doi.org/10.1039/C9GC02131K
Article type: Paper
Submitted: 25 Jun 2019
Accepted: 01 Aug 2019
First published: 01 Aug 2019

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Green Chem., 2019,21, 4706-4711

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Electrochemical oxidative cyclization of activated alkynes with diselenides or disulfides: access to functionalized coumarins or quinolinones

J. Hua, Z. Fang, J. Xu, M. Bian, C. Liu, W. He, N. Zhu, Z. Yang and K. Guo, Green Chem., 2019, 21, 4706 DOI: 10.1039/C9GC02131K

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Green Chemistry

Electrochemical oxidative cyclization of activated alkynes with diselenides or disulfides: access to functionalized coumarins or quinolinones†

Abstract

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Electrochemical oxidative cyclization of activated alkynes with diselenides or disulfides: access to functionalized coumarins or quinolinones

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