Journal of the American Chemical Society
Journal of the American Chemical Society
4 years ago

Palladium-Catalyzed Negishi Coupling of α-CF3 Oxiranyl Zincate: Access to Chiral CF3-Substituted Benzylic Tertiary Alcohols

Palladium-Catalyzed Negishi Coupling of α-CF3 Oxiranyl Zincate: Access to Chiral CF3-Substituted Benzylic Tertiary Alcohols
Stephen L. Buchwald, Hu Zhang
We report a Pd-catalyzed stereospecific α-arylation of optically pure 2,3-epoxy-1,1,1-trifluoropropane (TFPO). This method allows for the direct and reliable preparation of optically pure 2-CF3-2-(hetero)aryloxiranes, which are precursors to many CF3-substituted tertiary alcohols. The use of continuous-flow methods has allowed the deprotonation of TFPO and subsequent zincation at higher temperature compared to that under traditional batch conditions.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b06630

DOI: 10.1021/jacs.7b06630

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