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

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Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States
*[email protected]
Cite this: J. Am. Chem. Soc. 2017, 139, 33, 11590–11594
Publication Date (Web):July 28, 2017
https://doi.org/10.1021/jacs.7b06630
Copyright © 2017 American Chemical Society
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    Abstract

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    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.

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