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2,3-Disubstituted Benzo[b]thiophenes from Diarylalkynes via Electrophilic Addition-Cyclization and Palladium-Catalyzed Cross-Coupling
Article first published online: 11 SEP 2007
DOI: 10.1002/adsc.200700172
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Lamanna, G. and Menichetti, S. (2007), 2,3-Disubstituted Benzo[b]thiophenes from Diarylalkynes via Electrophilic Addition-Cyclization and Palladium-Catalyzed Cross-Coupling. Adv. Synth. Catal., 349: 2188–2194. doi: 10.1002/adsc.200700172
Publication History
- Issue published online: 18 SEP 2007
- Article first published online: 11 SEP 2007
- Manuscript Received: 4 APR 2007
Keywords:
- benzo[b]thiophenes;
- cross-coupling;
- electrophilic addition;
- electrophilic substitution;
- phthalimidesulfenyl chloride;
- solid phase synthesis
Abstract
Diarylalkynes are readily transformed in 3-chlorobenzo[b]thiophenes in a two-step electrophilic addition-cyclization procedure that runs highly efficiently in solution or in the solid phase. The heteroaromatic carbon-chlorine bond participates in palladium-catalyzed Suzuki–Miyaura or Buchwald–Hartwig cross-couplings to give, in a single step, 2,3-disubstituted derivatives of pharmacological relevance .