An Efficient Palladium-Catalyzed Synthesis of Cinnamaldehydes from Acrolein Diethyl Acetal and Aryl Iodides and Bromides

Gianfranco Battistuzzi, Sandro Cacchi,* and Giancarlo Fabrizi
Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Universit degli Studi La Sapienza, P. le A. Moro 5, 00185 Rome, Italy
Org. Lett., 2003, 5 (5), pp 777–780
DOI: 10.1021/ol034071p
Publication Date (Web): February 11, 2003
Copyright © 2003 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sandro.cacchi@uniroma1.it

Abstract

Abstract Image

The reaction of aryl iodides and bromides with acrolein diethyl acetal in the presence of Pd(OAc)2, nBu4NOAc, K2CO3, KCl, and DMF, at 90 °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.

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History

  • Published In Issue March 06, 2003
  • Received January 15, 2003

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