Palladium-catalyzed hydroarylation of alkynes with arenediazonium salts.
The palladium-catalyzed hydroarylation of arenediazonium tetrafluoroborates with alkynes in the presence of triphenylsilane affords stereoselectively hydroarylation products in moderate to high yields. The reaction tolerates a variety of substituents including keto, ester, cyano, and nitro groups and can be performed as a one-pot procedure generating the arenediazonium salt in situ. With ethyl phenylpropynoate as the starting alkyne, the hydroarylation affords ethyl (Z)-2-arylcinnamates stereo- and regioselectively.
Cacchi
Sandro
S
Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi La Sapienza, Piazzale A. Moro 5, 00185 Rome, Italy. sandro.cacchi@uniroma1.it
Fabrizi
Giancarlo
G
Goggiamani
Antonella
A
Persiani
Daniela
D
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
D000480:Alkynes; D003979:Diazonium Compounds; D010165:Palladium