title: Cu-Catalyzed Alkynylation of Unactivated C(sp(3))-X Bonds with Terminal Alkynes through Directing Strategy.
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.
authors.affiliation: Beijing National Laboratory of Molecule Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University , Beijing 100871, China.|State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences , Shanghai 200032, China.
authors.forename: Fei-Xian
authors.initials: FX
authors.lastname: Luo
authors.affiliation: Beijing National Laboratory of Molecule Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University , Beijing 100871, China.|State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences , Shanghai 200032, China.
authors.forename: Xing
authors.initials: X
authors.lastname: Xu
authors.affiliation: Beijing National Laboratory of Molecule Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University , Beijing 100871, China.|State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences , Shanghai 200032, China.
authors.forename: Ding
authors.initials: D
authors.lastname: Wang
authors.affiliation: Beijing National Laboratory of Molecule Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University , Beijing 100871, China.|State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences , Shanghai 200032, China.
authors.forename: Zhi-Chao
authors.initials: ZC
authors.lastname: Cao
authors.affiliation: Beijing National Laboratory of Molecule Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University , Beijing 100871, China.|State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences , Shanghai 200032, China.
authors.forename: Yun-Fei
authors.initials: YF
authors.lastname: Zhang
authors.affiliation: Beijing National Laboratory of Molecule Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University , Beijing 100871, China.|State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences , Shanghai 200032, China.
authors.forename: Zhang-Jie
authors.initials: ZJ
authors.lastname: Shi