Access to Difluoromethylene-Skipped 1,4-Diynes with gem-Difluoropropargyl Bromide

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• 作者：Wen-Hao Guo ; Zhi-Ji Luo ; Wenbin Zeng ; Xingang Zhang
• 刊名：ACS Catalysis
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：7
• 期：1
• 页码：896-901
• 全文大小：469K
• ISSN：2155-5435

文摘

Difluoromethylene (CF₂)-skipped 1,4-diynes are a versatile synthon in organic synthesis, but efficient methods to access such a fluorinated structural motif are very limited. Herein, we report an efficient method for catalytic synthesis of CF₂-skipped 1,4-diynes through palladium-catalyzed cross-coupling between terminal alkynes and gem-difluoropropargyl bromide. The reaction exhibits high functional group tolerance and broad substrate scope. Applications of the method led to a series of important difluorinated molecules that are of interest in medicinal chemistry.