Palladium-catalyzed cyclization of o-alkynyltrifluoroacetanilides followed by isocyanide insertion: synthesis of 2-substituted 1H-indole-3-carboxamides.
A base-controlled synthesis of 2-substituted secondary and tertiary 1H-indole-3-carboxamides through PdCl(2)-catalyzed cyclization of o-alkynyltrifluoroacetanilides followed by isocyanide insertion has been developed. The reaction proceeds smoothly at ambient temperature using O(2) in air as the sole oxidant of the palladium catalyst.
State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, China.
Ziwei
Z
Hu
Dongdong
D
Liang
Jiaji
J
Zhao
Jinbo
J
Huang
Qiang
Q
Zhu
D000083:Acetanilides / Q000737:chemistry*; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry*
D000083:Acetanilides; D003486:Cyanides; D007211:Indoles; D010165:Palladium; C008756:palladium chloride