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  • Title: Cu-Catalyzed Alkynylation of Unactivated C(sp(3))-X Bonds with Terminal Alkynes through Directing Strategy.
    Author: Luo FX, Xu X, Wang D, Cao ZC, Zhang YF, Shi ZJ.
    Journal: Org Lett; 2016 May 06; 18(9):2040-3. PubMed ID: 27074521.
    Abstract:
    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.
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