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

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Brambilla,  Marta
Research Group Tredwell, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Tredwell,  Matthew
Research Group Tredwell, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Brambilla, M., & Tredwell, M. (2017). Palladium Catalyzed Suzuki-Miyaura Cross-Coupling of Secondary α-(Trifluoromethyl)benzyl Tosylates. Angewandte Chemie International Edition in English, 56(39), 11981-11985. doi:10.1002/anie.201706631.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002D-B0E6-8
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.