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Issue 47, 2018
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Synthesis of 2-substituted benzo[b]thiophenes via gold(i)–NHC-catalyzed cyclization of 2-alkynyl thioanisoles

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Abstract

Benzo[b]thiophene heterocycles are important components of many important small molecule pharmaceuticals and drug candidates as well as organic semiconducting materials. Many methods have been developed for the construction of a benzo[b]thiophene core via cyclization reaction of alkynes. Although few catalytic reactions were disclosed, most methods rely on stoichiometric activation of alkynes. Here we report an efficient method for the synthesis of 2-substituted benzo[b]thiophenes from 2-alkynyl thioanisoles catalyzed by a gold(I)–IPr hydroxide that is applicable to a wide range of substrates with diverse electronic and steric properties. Additionally, we demonstrate experimentally that the acid additive and its conjugate base are essential to catalyst turnover.

Graphical abstract: Synthesis of 2-substituted benzo[b]thiophenes via gold(i)–NHC-catalyzed cyclization of 2-alkynyl thioanisoles

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Supplementary files

Article information


Submitted
06 Sep 2018
Accepted
16 Nov 2018
First published
16 Nov 2018

Org. Biomol. Chem., 2018,16, 9279-9284
Article type
Paper
Author version available

Synthesis of 2-substituted benzo[b]thiophenes via gold(I)–NHC-catalyzed cyclization of 2-alkynyl thioanisoles

C. C. Dillon, B. Keophimphone, M. Sanchez, P. Kaur and H. Muchalski, Org. Biomol. Chem., 2018, 16, 9279
DOI: 10.1039/C8OB02196A

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