4.7 Article

Copper Oxide Nanoparticle-Catalyzed Chalcogenation of the Carbon-Hydrogen Bond in Thiazoles: Synthesis of 2-(Organochalcogen)thiazoles

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 14-15, Pages 2960-2966

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300497

Keywords

carbon-hydrogen bond activation; copper; cross-coupling; selenides; thiazoles

Funding

  1. FAPERGS [PRONEX-10/0005-1]
  2. CAPES (SAUX)
  3. CNPq (CNPq/INCT-catalise)
  4. CNPq

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We present (homepage: www.ufsm.br) herein the application of copper nanoparticles/diorganyl dichalcogenides to promote the synthesis of 2-(organochalcogen)thiazoles via direct carbon-hydrogen bond activation in thiazoles. A systematic study of the catalytic system revealed that the presence and amount of base played an essential role in this reaction. The results revealed that electron-donating and electron-withdrawing substituents, in the aromatic ring bonded to the chalcogen atom of diorganyl dichalcogenides, required oneequiv. of base, while when neutral substituents were present twoequiv. of base were needed to deliver the products in similar yields.

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