Stereoconvergent Negishi Arylations of Racemic Secondary Alkyl Electrophiles: Differentiating between a CF₃ and an Alkyl Group

Yufan Liang and Gregory C. Fu*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, Email: gcfucaltech.edu

Y. Liang, G. C. Fu, J. Am. Chem. Soc., 2015, 137, 9523-9526.

DOI: 10.1021/jacs.5b04725

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Abstract

A readily available nickel/bis(oxazoline) catalyst effectively distinguishes between a CF₃ and an alkyl group and accomplishes a wide array of enantioconvergent cross-couplings of arylzinc reagents with CF₃-substituted racemic secondary alkyl halides. This method can also be applied without modification to the asymmetric synthesis of other families of fluorinated organic compounds.

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Key Words

Negishi coupling, benzylic trifluoromethanes, arylation

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ID: J48-Y2015