Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Secondary α-(Trifluoromethyl)benzyl Tosylates.

A palladium-catalyzed C(sp3 )-C(sp2 ) Suzuki-Miyaura cross-coupling of aryl boronic acids and α-(trifluoromethyl)benzyl tosylates is reported. A readily available, air-stable palladium catalyst was employed to access a wide range of functionalized 1,1-diaryl-2,2,2-trifluoroethanes. Enantioenriched α-(trifluoromethyl)benzyl tosylates were found to undergo cross-coupling to give the corresponding enantioenriched cross-coupled products with an overall inversion in configuration. The crucial role of the CF3 group in promoting this transformation is demonstrated by comparison with non-fluorinated derivatives.