Potassium Hydroxide/Dimethyl Sulfoxide Superbase-Promoted Transition Metal-Free Synthesis of 2-Substituted Benzothiophenes under Visible Light

Li Gao; Bin Chang; Wenzhao Qiu; Lele Wang; Xianzhi Fu; Rusheng Yuan

doi:10.1002/adsc.201501136

Potassium Hydroxide/Dimethyl Sulfoxide Superbase-Promoted Transition Metal-Free Synthesis of 2-Substituted Benzothiophenes under Visible Light

Li Gao, Bin Chang, Wenzhao Qiu, Lele Wang, Xianzhi Fu, Rusheng Yuan

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

34 Scopus citations

Abstract

A potassium hydroxide/dimethyl sulfoxide (KOH/DMSO) superbase-promoted method for the synthesis of 2-substituted benzothiophenes has been developed via photoinduced intermolecular annulation of 2-halothioanisoles with terminal alkynes at ambient temperature. The present protocol uses commercially available 2-halothioanisoles as substrates and visible light as energy force, which offers a wide range of benzothiophenes regioselectively in moderate to good yields. Such a facile and effective transformation will provide an environment-friendly approach to the synthesis of benzothiophene derivatives.

Original language	English (US)
Pages (from-to)	1202-1207
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	358
Issue number	8
DOIs	https://doi.org/10.1002/adsc.201501136
State	Published - Apr 14 2016

Bibliographical note

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

aryl radicals
benzothiophenes
photoinduced reaction
potassium hydroxide/dimethyl sulfoxide (KOH/DMSO) superbase
transition metal-free conditions

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201501136

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abstract = "A potassium hydroxide/dimethyl sulfoxide (KOH/DMSO) superbase-promoted method for the synthesis of 2-substituted benzothiophenes has been developed via photoinduced intermolecular annulation of 2-halothioanisoles with terminal alkynes at ambient temperature. The present protocol uses commercially available 2-halothioanisoles as substrates and visible light as energy force, which offers a wide range of benzothiophenes regioselectively in moderate to good yields. Such a facile and effective transformation will provide an environment-friendly approach to the synthesis of benzothiophene derivatives.",

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AU - Chang, Bin

AU - Qiu, Wenzhao

AU - Wang, Lele

AU - Fu, Xianzhi

AU - Yuan, Rusheng

PY - 2016/4/14

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AB - A potassium hydroxide/dimethyl sulfoxide (KOH/DMSO) superbase-promoted method for the synthesis of 2-substituted benzothiophenes has been developed via photoinduced intermolecular annulation of 2-halothioanisoles with terminal alkynes at ambient temperature. The present protocol uses commercially available 2-halothioanisoles as substrates and visible light as energy force, which offers a wide range of benzothiophenes regioselectively in moderate to good yields. Such a facile and effective transformation will provide an environment-friendly approach to the synthesis of benzothiophene derivatives.

KW - aryl radicals

KW - benzothiophenes

KW - photoinduced reaction

KW - potassium hydroxide/dimethyl sulfoxide (KOH/DMSO) superbase

KW - transition metal-free conditions

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Potassium Hydroxide/Dimethyl Sulfoxide Superbase-Promoted Transition Metal-Free Synthesis of 2-Substituted Benzothiophenes under Visible Light

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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