The Liebeskind-Srogl C-C Cross-Coupling Reaction

Although a plethora of highly selective and reliable methods for theconstruction of C-C bonds are known to organic chemists, there is growinginterest in the development of new protocols that offer different or orthogonalreactivity to that of existing methods. In 2000, Liebeskind and Srogl describeda mechanistically unprecedented transition-metal-catalyzed cross-coupling ofthioesters with boronic acids to produce ketones under neutral conditions. Thisdesulfitative cross-coupling process is catalytic in palladium(O),stoichiometric in copper(I), and applicable to a range of organosulfurderivatives and nucleophilic organometallic reagents. In this Minireview, wehighlight recent applications of this intriguing cross-coupling reaction inmodern organic synthesis, with an emphasis on cases in which traditional methodsfor C-C bond formation have failed. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.