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Synthesis of 2-substituted Benzo[b]thiophenes via gold(i)-NHC-catalyzed Cyclization of 2-alkynyl Thioanisoles

Synthesis of 2-substituted Benzo[b]thiophenes via gold(i)-NHC-catalyzed Cyclization of 2-alkynyl Thioanisoles

Christopher C Dillon, Bagieng Keophimphone, Melissa Sanchez, Parveen Kaur, Hubert Muchalski

Org Biomol Chem. 2018 Dec 5;16(47):9279-9284.

PMID: 30484460

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP98437231	Benzo[b]thien-2-ylboronic acid		98437-23-1	Price

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