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

H. Zhang and Buchwald, S. L. “Palladium-Catalyzed Negishi Coupling of α-CF3 Oxiranyl Zincate: Access to Chiral CF3-substituted Benzylic Tertiary Alcohols”, J. Am. Chem. Soc, 2017, 139, 11590-11594.

Abstract:

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.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.

Authors

Gary Zhang