2,3-Disubstituted indoles via palladium-catalyzed reaction of 2-alkynyltrifluoroacetanilides with arenediazonium tetrafluoroborates.
A novel palladium-catalyzed synthesis of free N-H 2,3-disubstituted indoles from arenediazonium tetrafluoroborates and 2-alkynyltrifluoroacetanilides is presented. The reaction tolerates a variety of useful substituents both in the starting alkyne and the arenediazonium salt, including bromo and chloro substituents, nitro, cyano, keto, ester, and ether groups, as well as ortho substituents such as methoxy and methyl groups.
Cacchi
Sandro
S
Dipartimento di Chimica e Tecnologie del Farmaco, La Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy. sandro.cacchi@uniroma1.it
Fabrizi
Giancarlo
G
Goggiamani
Antonella
A
Perboni
Alcide
A
Sferrazza
Alessio
A
Stabile
Paolo
P
D000083:Acetanilides / Q000737:chemistry*; D001881:Borates; D001888:Boric Acids / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry
D000083:Acetanilides; D001881:Borates; D001888:Boric Acids; D007211:Indoles; D011758:Pyrroles; D010165:Palladium; C098759:fluoroboric acid