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Direct Difluorination-Hydroxylation, Trifluorination, and C(sp2)-H Fluorination of Enamides
Socrates B Munoz1, Vinayak Krishnamurti1, Pablo Barrio2
1Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California , Los Angeles, California 90089, United States.
Abstract:
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 Brønsted 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.
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