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Free keywords:
cross-coupling; fluorine; homogeneous catalysis; palladium; transition-metal catalysis
Abstract:
A palladium catalyzed C(sp3)-C(sp2) Suzuki-Miyaura cross-coupling of aryl boronic acids and α-(trifluoromethyl)benzyl tosylates is reported. The reaction uses a readily available, air-stable palladium catalyst 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.
