Tetrahedron letters

Efficient synthesis of trisubstituted alkenes in an aqueous–organic system using a versatile and recyclable Rh/m-TPPTC catalyst

E Genin, V Michelet, JP Genêt

Index: Genin, Emilie; Michelet, Veronique; Genet, Jean-Pierre Tetrahedron Letters, 2004 , vol. 45, # 21 p. 4157 - 4161

Full Text: HTML

Citation Number: 51

Abstract

We have found that the use of [Rh (cod) OH] 2 associated with the water-soluble ligand m- TPPTC was highly efficient for the Rh-catalyzed arylation of alkynes. Aryl and alkyl alkynes were transformed to alkenes using 3mol% rhodium catalyst and 2.5 equiv of boronic acid at 100° C in a biphasic water/toluene system in 80–99% yield. The reaction was found to be totally regioselective for alkyl arylalkynes and alkyl silylated alkynes. The Rh/m-TPPTC ...