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Catalytic, Enantioselective 1,2-Difluorination of Cinnamamides

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journal contribution
posted on 09.04.2019, 00:00 authored by Moriana K. Haj, Steven M. Banik, Eric N. Jacobsen
The enantio- and diastereoselective synthesis of 1,2-difluorides via chiral aryl iodide-catalyzed difluorination of cinnamamides is reported. The method uses HF-pyridine as a fluoride source and mCPBA as a stoichiometric oxidant to turn over catalyst, and affords compounds containing vicinal, fluoride-bearing stereocenters. Selectivity for 1,2-difluorination versus a rearrangement pathway resulting in 1,1-difluorination is enforced through anchimeric assistance from a N-tert-butyl amide substituent.