Beilstein J. Org. Chem.2022,18, 1040–1046, doi:10.3762/bjoc.18.105
, Hokkaido 060-8628, Japan 10.3762/bjoc.18.105 Abstract Electrochemical Friedel–Crafts-typeamidomethylation was successfully carried out by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborates, such as iPr2NHEtBF4. Constant current electrolysis of
amidomethylated products in good to high yields.
Keywords: electrochemical oxidation; Friedel–Craftstypeamidomethylation; N-acyliminium ion; quasi-divided cell; trialkylammonium salt; Introduction
Oxidation of amides generates useful intermediates, N-acyliminium ions, which have been widely used in organic
synthesis [1][2][3][4]. For example, Friedel–Crafts-typeamidomethylation [5][6][7][8][9][10][11][12][13][14][15] proceeds efficiently by the reaction of N-acyliminium ions with electron-rich arenes to give the corresponding amidomethylated products in good yields. Since amides are important intermediates
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Graphical Abstract
Scheme 1:
Generation of N-acyliminium ion: previous and present works.