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. 2012 Mar 28;134(12):5524-7.
doi: 10.1021/ja301013h. Epub 2012 Mar 14.

Copper-mediated difluoromethylation of aryl and vinyl iodides

Patrick S Fier  1 , John F Hartwig
Affiliations

Copper-mediated difluoromethylation of aryl and vinyl iodides

Patrick S Fier et al. J Am Chem Soc. .

Abstract

Selectively fluorinated molecules are important as materials, pharmaceuticals, and agrochemicals, but their synthesis by simple, mild, laboratory methods is challenging. We report a straightforward method for the cross-coupling of aryl and vinyl iodides with a difluoromethyl group generated from readily available reagents to form difluoromethylarenes and difluoromethyl-substituted alkenes. The reaction of electron-neutral, electron-rich, and sterically hindered aryl and vinyl iodides with the combination of CuI, CsF and TMSCF(2)H leads to the formation of difluoromethyl-substituted products in high yield with good functional group compatibility. This transformation is surprising, in part, because of the prior observation of the instability of CuCF(2)H.

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Figures

Scheme 1
Scheme 1
Preparation of Difluoromethylarenes
Scheme 2
Scheme 2
Evidence against aryl and vinyl radical intermediates
See this image and copyright information in PMC

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