An efficient palladium-catalyzed synthesis of cinnamaldehydes from acrolein diethyl acetal and aryl iodides and bromides

Gianfranco Battistuzzi; Sandro Cacchi; Giancarlo Fabrizi

doi:10.1021/ol034071p

An efficient palladium-catalyzed synthesis of cinnamaldehydes from acrolein diethyl acetal and aryl iodides and bromides

Org Lett. 2003 Mar 6;5(5):777-80. doi: 10.1021/ol034071p.

Authors

Gianfranco Battistuzzi¹, Sandro Cacchi, Giancarlo Fabrizi

Affiliation

¹ Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi "La Sapienza", P. le A. Moro 5, 00185 Rome, Italy.

PMID: 12605513
DOI: 10.1021/ol034071p

Abstract

The reaction of aryl iodides and bromides with acrolein diethyl acetal in the presence of Pd(OAc)(2), (n)()Bu(4)NOAc, K(2)CO(3), KCl, and DMF, at 90 degrees C until the disappearance of the acetal followed by the addition of 2 N HCl to the crude reaction mixture, affords cinnamaldehydes in good to high yields. A variety of functional groups are tolerated in the aryl halides, including ether, aldehyde, ketone, ester, dialkylamino, nitrile, and nitro groups. The presence of substituents close to the oxidative addition site does not hamper the reaction.