A novel palladium-mediated coupling approach to 2,3-disubstituted benzo[b]thiophenes and its application to the synthesis of tubulin binding agents

Bernard L. Flynn, Pascal Verdier-Pinard, Ernest Hamel

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224 Citations (Scopus)

Abstract

Flexible, convergent access to 2,3-disubstituted benzo[b]thiophenes has been developed. The most concise approach involves sequential coupling of o-bromoiodobenzenes with benzylmercaptan and zinc acetylides to give benzyl o-ethynylpnenyl sulfides which react with iodine to give 3-iodobenzo[b]thiophenes in a 5-endo-dig iodocyclization. These iodides can be further elaborated using palladium-mediated coupling and/or metalation techniques. This method has been applied to the synthesis of some novel tubulin binding agents.

Original languageEnglish
Pages (from-to)651-653
Number of pages3
JournalOrganic Letters
Volume3
Issue number5
DOIs
Publication statusPublished - 8 Mar 2001
Externally publishedYes

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