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Solution-phase parallel synthesis of a multi-substituted benzo[b]thiophene library.

ABSTRACT: Generation of a library using parallel syntheses of multi-substituted benzo[b]thiophenes is described. The requisite 3-iodobenzo[b]thiophenes are readily prepared in excellent yields from various alkynes bearing electron-rich aromatic rings by electrophilic cyclization using I(2) in CH(2)Cl(2). The heteroaromatic carbon-iodine bonds allow further diversification by palladium-catalyzed Suzuki-Miyaura, Sonogashira, Heck, and carboalkoxylation chemistry to give multi-substituted benzo[b]thiophene derivatives.

SUBMITTER: Cho CH

PROVIDER: S-EPMC2743771 | biostudies-literature | 2009 Sep-Oct

REPOSITORIES: biostudies-literature

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Solution-phase parallel synthesis of a multi-substituted benzo[b]thiophene library.

Cho Chul-Hee CH Neuenswander Benjamin B Lushington Gerald H GH Larock Richard C RC

Journal of combinatorial chemistry 20090901 5

Generation of a library using parallel syntheses of multi-substituted benzo[b]thiophenes is described. The requisite 3-iodobenzo[b]thiophenes are readily prepared in excellent yields from various alkynes bearing electron-rich aromatic rings by electrophilic cyclization using I(2) in CH(2)Cl(2). The heteroaromatic carbon-iodine bonds allow further diversification by palladium-catalyzed Suzuki-Miyaura, Sonogashira, Heck, and carboalkoxylation chemistry to give multi-substituted benzo[b]thiophene d ...[more]

PMID: 19569714

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