title: Copper-Catalyzed Cyclopropanol Ring Opening Csp(3)-Csp(3) Cross-Couplings with (Fluoro)Alkyl Halides.
abstract: Novel and general copper-catalyzed cyclopropanol ring opening cross-coupling reactions with difluoroalkyl bromides, perfluoroalkyl iodides, monofluoroalkyl bromides, and 2-bromo-2-alkylesters to synthesize various β-(fluoro)alkylated ketones are reported. The reactions feature mild conditions and excellent functional group compatibility and can be scaled up to gram scale. Preliminary mechanistic studies suggest the involvement of radical intermediates. The difluoroalkyl-alkyl cross-coupling products can also be readily converted to more valuable and diverse gem-difluoro-containing compounds by taking advantage of the carbonyl group resulting from cyclopropanol ring opening.
authors.affiliation: Department of Chemistry and Center for Cancer Research, Purdue University , 560 Oval Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Zhishi
authors.initials: Z
authors.lastname: Ye
authors.affiliation: Department of Chemistry and Center for Cancer Research, Purdue University , 560 Oval Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Kristen E
authors.initials: KE
authors.lastname: Gettys
authors.affiliation: Department of Chemistry and Center for Cancer Research, Purdue University , 560 Oval Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Xingyu
authors.initials: X
authors.lastname: Shen
authors.affiliation: Department of Chemistry and Center for Cancer Research, Purdue University , 560 Oval Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Mingji
authors.initials: M
authors.lastname: Dai
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D004988:Ethers, Cyclic; D006842:Hydrocarbons, Brominated; D006845:Hydrocarbons, Fluorinated; D007454:Iodides; C043657:cyclopropanol; D003300:Copper; C073870:cuprous iodide