title: Catalytic, Diastereoselective 1,2-Difluorination of Alkenes.
abstract: We describe a direct, catalytic approach to the 1,2-difluorination of alkenes. The method utilizes a nucleophilic fluoride source and an oxidant in conjunction with an aryl iodide catalyst and is applicable to alkenes with all types of substitution patterns. In general, the vicinal difluoride products are produced with high diastereoselectivities. The observed sense of stereoinduction implicates anchimeric assistance pathways in reactions of alkenes bearing neighboring Lewis basic functionality.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors.forename: Steven M
authors.initials: SM
authors.lastname: Banik
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors.forename: Jonathan William
authors.initials: JW
authors.lastname: Medley
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors.forename: Eric N
authors.initials: EN
authors.lastname: Jacobsen
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D006845:Hydrocarbons, Fluorinated