title: Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation.
abstract: The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42-84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3-32h to 10-70min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.
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: Mercedes A
authors.initials: MA
authors.lastname: Badajoz
authors.forename: Claudia
authors.initials: C
authors.lastname: Domini
authors.forename: Alicia B
authors.initials: AB
authors.lastname: Chopa
authors.forename: María T
authors.initials: MT
authors.lastname: Lockhart
mesh_terms: D002384:Catalysis; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry; D007204:Indium / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D015394:Molecular Structure; D013010:Sonication; D013016:Sound; D017971:Tin Compounds / Q000737:chemistry* / Q000528:radiation effects
chemical_list: D006843:Hydrocarbons, Chlorinated; D007659:Ketones; D017971:Tin Compounds; D007204:Indium; C031525:stannane