title: Nickel-catalyzed chelation-assisted transformations involving ortho C-H bond activation: regioselective oxidative cycloaddition of aromatic amides to alkynes.
abstract: Although the pioneering example of ortho metalation involving cleavage of C-H bonds was achieved using a nickel complex (Kleiman, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 85, 1544), no examples of catalysis using nickel complexes have been reported. In this work, the Ni-catalyzed transformation of ortho C-H bonds utilizing chelation assistance, such as oxidative cycloaddition of aromatic amides with alkynes, has been achieved.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka, Japan.
authors.forename: Hirotaka
authors.initials: H
authors.lastname: Shiota
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Ano
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Aihara
authors.forename: Yoshiya
authors.initials: Y
authors.lastname: Fukumoto
authors.forename: Naoto
authors.initials: N
authors.lastname: Chatani
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D002614:Chelating Agents / Q000737:chemistry*; D003500:Cyclization; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000577:Amides; D002614:Chelating Agents; D007546:Isoquinolines; D009942:Organometallic Compounds; D009532:Nickel