title: Construction of C(aryl)-C(alkynyl) bond from copper-mediated arene-alkyne and aryl iodide-alkyne cross-coupling reactions: a common aryl-Cu(III) intermediate in arene C-H activation and Castro-Stephens reaction.
abstract: Both copper(II)-mediated oxidative C-H bond activation and oxidative addition of copper(I) into a C-I bond produced an identical and structurally well-defined aryl-Cu(III) intermediate. The cross-coupling reaction of an aryl-Cu(III) intermediate with both terminal alkynes at an elevated temperature and alkynyllithium reagents under mild conditions led effectively to the formation of a C(aryl)-C(alkynyl) bond. An alternative mechanism has been proposed for the Castro-Stephens reaction.
authors.affiliation: MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing 100084, China.
authors.forename: Zu-Li
authors.initials: ZL
authors.lastname: Wang
authors.forename: Liang
authors.initials: L
authors.lastname: Zhao
authors.forename: Mei-Xiang
authors.initials: MX
authors.lastname: Wang
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D011725:Pyridines / Q000737:chemistry*
chemical_list: D000480:Alkynes; D006847:Hydrocarbons, Iodinated; D009942:Organometallic Compounds; D011725:Pyridines; D003300:Copper