Organic Letters 2004-05-13

Sterically bulky thioureas as air- and moisture-stable ligands for pd-catalyzed Heck reactions of aryl halides.

Dan Yang, Ying-Chun Chen, Nian-Yong Zhu

Index: Org. Lett. 6 , 1577, (2004)

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Abstract

We demonstrate that sterically bulky N,N'-disubstituted cyclic thiourea-Pd(0) complexes are air- and moisture-stable and highly active catalysts for palladium-catalyzed Heck reaction of aryl iodides and bromides with olefins (TONs up to 500000 for the reaction of PhI and methyl acrylate). Even activated aryl chlorides can undergo complete conversion in Bu(4)NBr in the presence of 1 mol % Pd catalyst.