4.7 Article

Synthesis of 2,3-Diarylbenzo[b]thiophenes via Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling and Palladium-Catalyzed Decarboxylative Arylation

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 16, Pages 2683-2688

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900480

Keywords

arylation; benzothiophenes; nickel; palladium

Funding

  1. Ministry of Education, Culture, Sports, Science, and Technology, Japan
  2. JSPS

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We report a new approach to 2,3-diarylbenzo[b]thiophenes based on the nickel-catalyzed Suzuki-Miyaura cross-coupling/palladium-catalyzed decarboxylative arylation sequence of 3-chloro-2-methoxycarbonylbenzo[b]thiophenes, which are readily accessible from the corresponding cinnamic acids. In addition, this methodology can be applied to the concise synthesis of pi-extended 2,3,6,7-tetraarylbenzo[1,2-b;4,5-b']dithiophenes. Their optical properties are also described.

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