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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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Publication details

The article was received on 06 Sep 2018, accepted on 16 Nov 2018 and first published on 16 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02196A
Citation: Org. Biomol. Chem., 2018,16, 9279-9284
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    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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