title: Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes.
abstract: Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl(3) (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.
authors.affiliation: Instituto de Química del Sur (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, Bahía Blanca, B8000CPB, Argentina.
authors.forename: Marcos J
authors.initials: MJ
authors.lastname: Lo Fiego
authors.forename: Gustavo F
authors.initials: GF
authors.lastname: Silbestri
authors.forename: Alicia B
authors.initials: AB
authors.lastname: Chopa
authors.forename: María T
authors.initials: MT
authors.lastname: Lockhart
mesh_terms: D002384:Catalysis; D002722:Chlorobenzenes / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D007204:Indium / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D013379:Substrate Specificity; D017971:Tin Compounds / Q000737:chemistry*
chemical_list: D002722:Chlorobenzenes; D007202:Indicators and Reagents; D007659:Ketones; D017971:Tin Compounds; D007204:Indium; C031525:stannane; C031294:chlorobenzene