Electroreductive acylation of aromatic ketones with acylimidazoles.
[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.
Kise
Naoki
N
Department of Biotechnology, Faculty of Engineering, Tottori University, Koyama, Tottori 680-8552, Japan. kise@bio.tottori-u.ac.jp
Agui
Syun
S
Morimoto
Shinji
S
Ueda
Nasuo
N
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
D004952:Esters; D006841:Hydrocarbons, Aromatic; D007093:Imidazoles; D007659:Ketones; D014297:Trimethylsilyl Compounds; D005680:gamma-Aminobutyric Acid; D010165:Palladium; C039293:trimethylchlorosilane