Organic Letters 2011-12-16

The palladium-catalyzed trifluoromethylation of vinyl sulfonates.

Eun Jin Cho, Stephen L Buchwald

Index: Org. Lett. 13(24) , 6552-5, (2011)

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Abstract

A method for the palladium-catalyzed trifluoromethylation of cyclohexenyl sulfonates has been developed. Various cyclohexenyl triflates and nonaflates underwent trifluoromethylation under mild reaction conditions using a catalyst system composed of Pd(dba)(2) or [(allyl)PdCl](2) and the monodentate biaryl phosphine ligand (t)BuXPhos. The trifluoromethyl anion (CF(3)(-)) or its equivalent for the process was generated in situ from TMSCF(3) in combination with KF or TESCF(3) in combination with RbF.