title: Nucleophilic bromodifluoromethylation of iminium ions.
abstract: A method for bromodifluoromethylation of iminium ions using Me3SiCF2Br is described. The reaction involves room temperature activation of the silicon reagent by HMPA to generate difluorocarbene, which upon interacting with excess of bromide ion provides bromodifluoromethyl carbanionic species. The iminium electrophiles are generated in situ from aldehydes, secondary amines, proton sponge, and silyl triflate. The reaction can be extended for introduction of chlorodifluoromethyl and iododifluoromethyl groups.
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry , 119991 Moscow, Leninsky prosp. 47, Russian Federation.
authors.forename: Artem V
authors.initials: AV
authors.lastname: Tsymbal
authors.forename: Mikhail D
authors.initials: MD
authors.lastname: Kosobokov
authors.forename: Vitalij V
authors.initials: VV
authors.lastname: Levin
authors.forename: Marina I
authors.initials: MI
authors.lastname: Struchkova
authors.forename: Alexander D
authors.initials: AD
authors.lastname: Dilman