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  • Title: Electroreductive acylation of aromatic ketones with acylimidazoles.
    Author: Kise N, Agui S, Morimoto S, Ueda N.
    Journal: J Org Chem; 2005 Nov 11; 70(23):9407-10. PubMed ID: 16268614.
    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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