6533b7d8fe1ef96bd126b576

RESEARCH PRODUCT

Direct Difluorination–Hydroxylation, Trifluorination, and C(sp2)–H Fluorination of Enamides

Thomas MathewG. K. Surya PrakashSocrates B. MunozVinayak KrishnamurtiPablo Barrio

subject

010405 organic chemistryOrganic Chemistry010402 general chemistry01 natural sciencesBiochemistryCombinatorial chemistry0104 chemical sciencesHydroxylationchemistry.chemical_compoundchemistryReagentElectrophileSurface modificationPhysical and Theoretical Chemistry

description

A direct double functionalization involving both difluorination and hydroxylation of enamides is reported. With the appropriate combination of an electrophilic fluorinating reagent and H2O, the most convenient and ecofriendly hydroxylating agent, the preparation of 3-(difluoroalkyl)-3-hydroxyisoindolin-1-ones was achieved under basic or Bronsted acidic conditions. Suitable conditions for trifluorination as well as C(sp2)–H fluorination were also identified. Subsequent asymmetric functionalization of the obtained gem-difluorinated products has also been demonstrated.

yearjournalcountryeditionlanguage
2018-01-31Organic Letters
https://doi.org/10.1021/acs.orglett.7b03994