Nucleophilic Iododifluoromethylation of Aldehydes Using Bromine/Iodine Exchange

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• 作者：Vitalij V. Levin ; Vladimir O. Smirnov ; Marina I. Struchkova ; Alexander D. Dilman
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：September 18, 2015
• 年：2015
• 卷：80
• 期：18
• 页码：9349-9353
• 全文大小：332K
• ISSN：1520-6904

文摘

A method for the iododifluoromethylation of aromatic aldehydes using (bromodifluoromethyl)trimethylsilane (Me₃SiCF₂Br) is described. The selective formation of the CF₂I group is based on using sodium iodide, with the sodium serving as a scavenger of bromide and iodide serving as a nucleophile with respect to difluorocarbene. The primary CF₂I-addition products can undergo HI-elimination or iodine/zinc exchange followed by allylation in a one-pot manner.