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A Novel Palladium-Mediated Coupling Approach to 2,3-Disubstituted Benzo[ b ]thiophenes and Its Application to the Synthesis of Tubulin Binding Agents

Flynn, Bernard; Verdier-Pinard, Pascal; Hamel, Ernest


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...[Show more]

CollectionsANU Research Publications
Date published: 2001
Type: Journal article
Source: Organic Letters
DOI: 10.1021/ol0067179


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