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A one-pot successive cyclization-alkylation strategy for the synthesis of 2,3-disubstituted benzo[ b ]thiophenes
Journal article   Peer reviewed

A one-pot successive cyclization-alkylation strategy for the synthesis of 2,3-disubstituted benzo[ b ]thiophenes

Christopher Cunningham, Matthew Cloyd, Aimee Phillips, Soha Khan, Katherine Whalen and Tanay Kesharwani
Organic & biomolecular chemistry, Vol.19(18), pp.4107-4117
05/12/2021
DOI: https://doi.org/10.1039/d1ob00358e
PMCID: PMC8211089
PMID: 33978029
Web of Science ID: WOS:000640679700001

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Abstract

In this study, a new environmentally benign iodine-mediated one-pot iodocyclization/alkylation strategy for the synthesis of benzo[b]thiophene derivatives starting from 2-alkynylthioanisoles was developed. The synthesis of a diverse population of 2,3-disubstituted benzo[b]thiophenes was achieved in high yields by employing moderate reaction conditions using 1,3-dicarbonyl substrates as the nucleophile and various substituted propargyl alcohols as both the cyclization precursor and the alkylating agent. This method resulted in the formation of a series of complex structures obtained in a single step. Additionally, a strategy was devised for the one pot iodocyclization/oxidation of propargyl alcohols into carbonyl functionalized benzo[b]thiophene structures. These green one-pot reaction processes were designed to reduce wastes and byproducts while generating a complex substitution pattern on the benzo[b]thiophene structure. The reported methodologies may be used to synthesize more functionalized benzo[b]thiophene structures that can be used in both biomedical and organic electronic applications.

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