Electroreductive acylation of aromatic ketones with acylimidazoles |
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Authors: | Kise Naoki Agui Syun Morimoto Shinji Ueda Nasuo |
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Affiliation: | Department of Biotechnology, Faculty of Engineering, Tottori University, Koyama, Tottori 680-8552, Japan. kise@bio.tottori-u.ac.jp |
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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. |
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