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

Abdellaoui Fatma; Youssef Chiraz; Ben Ammar Hamed; Soule Jean Francois; Doucet Henri<sup>*</sup>

doi:10.1055/s-0034-1379021

登录

免费注册

赞收藏引用

科研之友

微信

新浪微博

Facebook

分享链接

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

作者：Abdellaoui Fatma; Youssef Chiraz; Ben Ammar Hamed; Soule Jean Francois; Doucet Henri^*

来源：Synthesis (Germany), 2014, 46(24): 3341-3350.

DOI：10.1055/s-0034-1379021

摘要

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.