Efficient synthesis of trisubstituted alkenes in an aqueous–organic system using a versatile and recyclable Rh/ m -TPPTC catalyst
2004; Elsevier BV; Volume: 45; Issue: 21 Linguagem: Inglês
10.1016/j.tetlet.2004.03.136
ISSN1873-3581
AutoresEmilie Génin, Véronique Michelet, Jean‐Pierre Genêt,
Tópico(s)Organoboron and organosilicon chemistry
ResumoWe 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 3 mol % 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 system was for the first time recycled with no loss of the activity and with excellent purity of the desired alkene.
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