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Radical Chlorodifluoromethylation: Providing a Motif for (Hetero)arene Diversification.

ABSTRACT: A method for the radical chlorodifluoromethylation of (hetero)arenes using chlorodifluoroacetic anhydride is reported. This operationally simple protocol proceeds under mild photochemical conditions with high functional group compatibility and complements the large body of literature for the trifluoromethylation of (hetero)arenes. Introduction of the chlorodifluoromethyl motif enables rapid diversification to a wide array of aromatic scaffolds. This work showcases the chlorodifluoromethyl group as an attractive entryway to otherwise synthetically challenging electron-rich difluoromethyl(hetero)arenes. Furthermore, facile conversion of the CF2Cl moiety into the corresponding aryl esters, gem-difluoroenones, and ?-keto-esters is demonstrated.

SUBMITTER: McAtee RC

PROVIDER: S-EPMC6011751 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Radical Chlorodifluoromethylation: Providing a Motif for (Hetero)arene Diversification.

McAtee Rory C RC Beatty Joel W JW McAtee Christopher C CC Stephenson Corey R J CRJ

Organic letters 20180601 12

A method for the radical chlorodifluoromethylation of (hetero)arenes using chlorodifluoroacetic anhydride is reported. This operationally simple protocol proceeds under mild photochemical conditions with high functional group compatibility and complements the large body of literature for the trifluoromethylation of (hetero)arenes. Introduction of the chlorodifluoromethyl motif enables rapid diversification to a wide array of aromatic scaffolds. This work showcases the chlorodifluoromethyl group ...[more]

PMID: 29856642

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