Difluoromethylation of aryl and vinyl iodides

US9475756B2 · kind B2 · utility

Assignee

• The Regents of the University of California · US

Inventors

• John F. Hartwig · Durham, US
• Patrick Fier · Berkeley, US

Key dates

• Filing date: Mar 5, 2013
• Grant date: Oct 25, 2016
• Expiry date: Mar 5, 2033

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07B2200/09
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

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 a difluoromethyl group with readily available reagents to form difluoromethylarenes. The reaction of electron-neutral, electron rich, and sterically hindered aryl and vinyl iodides with the combination of CuI, CsF and TMSCF2H leads to the formation of difluoromethylarenes in high yield with good functional group compatibility. This transformation is surprising, in part, because of the prior observation of the instability of CuCF2H.