Nucleophilic Bromodifluoromethylation of Iminium Ions

作者:Tsymbal Artem V; Kosobokov Mikhail D; Levin Vitalij V; Struchkova Marina I; Dilman Alexander D*
来源:Journal of Organic Chemistry, 2014, 79(17): 7831-7835.
DOI:10.1021/jo501644m

摘要

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.

  • 出版日期2014-9-5