Cu-Catalyzed Alkynylation of Unactivated C(sp3)–X Bonds with Terminal Alkynes through Directing Strategy

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• 作者：Fei-Xian Luo ; Xing Xu ; Ding Wang ; Zhi-Chao Cao ; Yun-Fei Zhang ; Zhang-Jie Shi
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：18
• 期：9
• 页码：2040-2043
• 全文大小：395K
• 年卷期：0
• ISSN：1523-7052

文摘

In this letter, we report an efficient and concise protocol for Cu-catalyzed cross-coupling of unactivated alkyl halides/peusudohalides with terminal alkynes to afford internal alkynes with the assistance of various amides as directing groups. Different alkyl halides/pseudohalides exhibited excellent reactivities, and the inactivated alkyl chlorides and sulfonates showed better reactivity than bromides/iodides. This is the first successful example to apply alkyl chlorides and sulfonates directly in cross-coupling with terminal alkynes in the absence of any additives. A Cu catalyst was found to be more effective than other transition metal catalysts. This reaction also exhibited a broad substrate scope with respect to terminal alkynes.