title: Copper(I)-catalyzed alkylation of polyfluoroarenes through Direct C-H bond functionalization.
abstract: The copper(I)-catalyzed alkylation of electron-deficient polyfluoroarenes with N-tosylhydrazones and diazo compounds has been developed. This reaction uses readily available starting materials and is operationally simple, thus representing a practical method for the construction of C(sp(2) )-C(sp(3) ) bonds with polyfluoroarenes through direct C-H bond functionalization. Mechanistically, copper(I) carbene formation and subsequent migratory insertion are proposed as the key steps in the reaction pathway.
authors.affiliation: Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China).
authors.forename: Shuai
authors.initials: S
authors.lastname: Xu
authors.forename: Guojiao
authors.initials: G
authors.lastname: Wu
authors.forename: Fei
authors.initials: F
authors.lastname: Ye
authors.forename: Xi
authors.initials: X
authors.lastname: Wang
authors.forename: Huan
authors.initials: H
authors.lastname: Li
authors.forename: Xia
authors.initials: X
authors.lastname: Zhao
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhang
authors.forename: Jianbo
authors.initials: J
authors.lastname: Wang
mesh_terms: D000478:Alkylation; D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004583:Electrons; D005461:Fluorine / Q000737:chemistry*; D054879:Halogenation; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D014105:Tosyl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001391:Azo Compounds; D006835:Hydrazones; D006841:Hydrocarbons, Aromatic; D014105:Tosyl Compounds; C030011:carbene; D005461:Fluorine; D003300:Copper; D008697:Methane
keywords: CH activation; carbenes; copper; diazo compounds; synthetic methods