Synthesis of substituted carbazoles by a vinylic to aryl palladium migration involving domino C-H activation processes.
Substituted carbazoles are readily prepared in good yields by the palladium-catalyzed cross-coupling of alkynes and N-(3-iodophenyl)anilines. This process proceeds by carbopalladation of the alkyne, heteroatom-directed vinylic to aryl palladium migration, and ring closure involving two consecutive C-H activation processes. The process has also been expanded to the synthesis of an indole. [Structure: see text]
Zhao
Jian
J
Department of Chemistry, Iowa State University, Ames, IA 50011, USA.
Larock
Richard C
RC
D000480:Alkynes / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis*; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D010165:Palladium; D014753:Vinyl Compounds / Q000737:chemistry*
D000480:Alkynes; D002227:Carbazoles; D014753:Vinyl Compounds; D010165:Palladium