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Copper-mediated difluoromethylation of aryl and vinyl iodides.

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.

SUBMITTER: Fier PS

PROVIDER: S-EPMC3324264 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

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Copper-mediated difluoromethylation of aryl and vinyl iodides.

Fier Patrick S PS Hartwig John F JF

Journal of the American Chemical Society 20120314 12

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 c ...[more]

PMID: 22397683

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