title: Electroreductive acylation of aromatic ketones with acylimidazoles.
abstract: [Reaction: see text]. The intermolecular reductive coupling of aromatic ketones with acylimidazoles was effected by electroreduction in the presence of chlorotrimethylsilane and gave alpha-trimethylsiloxy ketones and esters. The best result was obtained using Bu4NPF6 as a supporting electrolyte and a Pb cathode in THF. The alpha-trimethylsiloxy-containing products were transformed to the corresponding alpha-hydroxy ketones and esters by treatment with TBAF in THF. This method was also effective for the intramolecular reductive coupling of delta- and epsilon-keto acylimidazoles.
authors.affiliation: Department of Biotechnology, Faculty of Engineering, Tottori University, Koyama, Tottori 680-8552, Japan. kise@bio.tottori-u.ac.jp
authors.forename: Naoki
authors.initials: N
authors.lastname: Kise
authors.forename: Syun
authors.initials: S
authors.lastname: Agui
authors.forename: Shinji
authors.initials: S
authors.lastname: Morimoto
authors.forename: Nasuo
authors.initials: N
authors.lastname: Ueda
mesh_terms: D000215:Acylation; D004566:Electrodes; D004952:Esters / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry; D005680:gamma-Aminobutyric Acid
chemical_list: D004952:Esters; D006841:Hydrocarbons, Aromatic; D007093:Imidazoles; D007659:Ketones; D014297:Trimethylsilyl Compounds; D005680:gamma-Aminobutyric Acid; D010165:Palladium; C039293:trimethylchlorosilane