Baylis-Hillman adducts in rhodium-catalyzed 1,4-additions: unusual reactivity.

Chem Commun (Camb)

Laboratoire de Synthese Selective Organique, UMR 7573, CNRS, Ecole Nationale Superieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05, France.

Published: May 2004

AI Article Synopsis

  • The study shows that unactivated Baylis-Hillman adducts can react with arylboronic acids in the presence of a rhodium catalyst to create trisubstituted alkenes effectively.
  • The reaction is efficient, occurring under aerobic conditions and at low temperatures.
  • It is suggested that the mechanism involves 1,4-addition and beta-hydroxy elimination, instead of the conventional pi-allyl type intermediates associated with rhodium catalysts.

Article Abstract

In the presence of a rhodium catalyst, unactivated Baylis-Hillman adducts reacted with arylboronic acids to afford trisubstituted alkenes with good yields. This highly efficient reaction (aerobic conditions, low temperature) is believed to proceeds via an unexpected mechanism involving 1,4-addition/beta-hydroxy elimination steps and not pi-allyl type rhodium intermediates.

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http://dx.doi.org/10.1039/b402928cDOI Listing

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