Copper-catalyzed domino synthesis of benzo[b]thiophene/imidazo[1,2-a]pyridines by sequential Ullmann-type coupling and intramolecular C(sp2)–H thiolation

Kelu Yan; Daoshan Yang; Wei Wei; Shenglei Lu; Guoqing Li; Caixia Zhao; Qingyun Zhang; Hua Wang

doi:10.1039/C5QO00311C

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Copper-catalyzed domino synthesis of benzo[b]thiophene/imidazo[1,2-a]pyridines by sequential Ullmann-type coupling and intramolecular C(sp²)–H thiolation†

Kelu Yan,^a Daoshan Yang,*^a Wei Wei,^a Shenglei Lu,^a Guoqing Li,^a Caixia Zhao,^a Qingyun Zhang^a and Hua Wang*^a

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* Corresponding authors

^a The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. China
E-mail: yangdaoshan@tsinghua.org.cn, huawang_qfnu@126.com

Abstract

The copper-catalyzed double C–S bond formation via Ullmann-type S-arylation and C–H thiolation using K₂S as a sulfur source is described. This novel one-step sulfur-incorporation method provides a straightforward avenue to benzo[b]thiophene and imidazo[1,2-a]pyridine frameworks.

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Article information

DOI: https://doi.org/10.1039/C5QO00311C
Article type: Research Article
Submitted: 10 Oct 2015
Accepted: 14 Nov 2015
First published: 17 Nov 2015

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Org. Chem. Front., 2016,3, 66-70

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Copper-catalyzed domino synthesis of benzo[b]thiophene/imidazo[1,2-a]pyridines by sequential Ullmann-type coupling and intramolecular C(sp²)–H thiolation

K. Yan, D. Yang, W. Wei, S. Lu, G. Li, C. Zhao, Q. Zhang and H. Wang, Org. Chem. Front., 2016, 3, 66 DOI: 10.1039/C5QO00311C

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