Nucleophilic Bromodifluoromethylation of Iminium Ions

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• 作者：Artem V. Tsymbal ; Mikhail D. Kosobokov ; Vitalij V. Levin ; Marina I. Struchkova ; Alexander D. Dilman
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：September 5, 2014
• 年：2014
• 卷：79
• 期：17
• 页码：7831-7835
• 全文大小：289K
• ISSN：1520-6904

文摘

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.