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Synthesis 2014; 46(24): 3341-3350
DOI: 10.1055/s-0034-1379021
DOI: 10.1055/s-0034-1379021
paper
A Simple and Efficient Synthesis of (Hetero)Aryl-Substituted Benzothiazolyl or Benzoxazolyl Furan, Thiophene and N-methylpyrrole Derivatives through a Palladium-Catalyzed Regioselective C–H Bond Arylation
Weitere Informationen
Publikationsverlauf
Received: 13. Juni 2014
Accepted after revision: 04. August 2014
Publikationsdatum:
10. September 2014 (online)
Abstract
The synthesis of 2-(hetero)aryl-5-benzothiazol-2-yl or -benzoxazol-2-ylfuran, -thiophene, and -1-methylpyrrole derivatives was accomplished in two steps. 2-(Benzothiazol-2-yl)- or 2-benzoxazol-2-ylfuran, -thiophene, or -1-methylpyrrole were synthesized by coupling a heteroaryl aldehyde and either 2-mercaptophenol or 2-aminophenol. Then, they were successfully arylated with a wide range of aryl bromides using a phosphine-free palladium protocol; regioselective arylation at C5 of furan, thiophene, or 1-methyl-1H-pyrrole was observed in all cases. This reaction tolerates a wide variety of substituents on the aryl bromides as well as heteroaryl bromides.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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