title: Halogenative difluorohomologation of ketones.
abstract: A method for the difluorohomologation of ketones accompanied by halogenation of a C-H bond is described. The reaction involves silylation, difluorocarbene addition using Me3SiCF2Br activated by a bromide ion, and halogenation of intermediate cyclopropanes with N-bromo- or N-iodosuccinimide. The whole process is performed without isolation of intermediates. The resulting α,α-difluoro-β-halo-substituted ketones can be readily converted into fluorine containing pyrazole derivatives and oxetanes.
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation.
authors.forename: Oleg V
authors.initials: OV
authors.lastname: Fedorov
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation.
authors.forename: Mikhail D
authors.initials: MD
authors.lastname: Kosobokov
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation.
authors.forename: Vitalij V
authors.initials: VV
authors.lastname: Levin
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation.
authors.forename: Marina I
authors.initials: MI
authors.lastname: Struchkova
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation.
authors.forename: Alexander D
authors.initials: AD
authors.lastname: Dilman
mesh_terms: D001974:Bromosuccinimide / Q000737:chemistry; D002384:Catalysis; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D006860:Hydrogen Bonding; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013388:Succinimides / Q000737:chemistry
chemical_list: D004988:Ethers, Cyclic; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D011720:Pyrazoles; D013388:Succinimides; C008155:N-iodosuccinimide; C005287:oxetane; D001974:Bromosuccinimide