Direct Nucleophilic Difluoromethylation of Carbonyl Compounds

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• 作者：Zuyong Deng ; Jin-Hong Lin ; Ji Cai ; Ji-Chang Xiao
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：18
• 期：13
• 页码：3206-3209
• 全文大小：300K
• 年卷期：0
• ISSN：1523-7052

文摘

Phosphonium salt ([Ph₃P⁺CF₂H] Br^–, DFPB) was found to be an efficient nucleophilic difluoromethylation reagent. Although DFPB is known as a phosphonium ylide precursor, its reaction with carbonyl compounds under traditional “Wittig reaction conditions” did not give the expected Wittig difluoroolefinated products, but afforded the nucleophilic difluoromethylation products, α-CF₂H alcohols. Mechanistic investigation reveals that the unexpected transformation proceeded via the direct transfer of the CF₂H group, which resulted from the high P–O affinity.