title: Experimental and mechanistic analysis of the palladium-catalyzed oxidative C8-selective C-H homocoupling of quinoline N-oxides.
abstract: A novel site-selective palladium-catalyzed oxidative C8-H homocoupling reaction of quinoline N-oxides has been developed. The reaction affords substituted 8,8'-biquinolyl N,N'-dioxides that can be readily converted to a variety of functionalized 8,8'-biquinolyls. Mechanistic studies point to the crucial role of the oxidant and a non-innocent behavior of acetic acid as a solvent.
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, San Antonio, TX 78249, USA. oleg.larionov@utsa.edu.
authors.forename: David E
authors.initials: DE
authors.lastname: Stephens
authors.forename: Johant
authors.initials: J
authors.lastname: Lakey-Beitia
authors.forename: Gabriel
authors.initials: G
authors.lastname: Chavez
authors.forename: Carla
authors.initials: C
authors.lastname: Ilie
authors.forename: Hadi D
authors.initials: HD
authors.lastname: Arman
authors.forename: Oleg V
authors.initials: OV
authors.lastname: Larionov
mesh_terms: D019342:Acetic Acid / Q000737:chemistry; D002384:Catalysis; D016877:Oxidants / Q000737:chemistry; D058451:Oxidative Coupling; D010087:Oxides / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: D016877:Oxidants; D010087:Oxides; D011804:Quinolines; D012997:Solvents; D014867:Water; D010165:Palladium; D019342:Acetic Acid