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-type amidomethylation was successfully carried out by a novel electrochemical oxidation system using a quasi-dividedcell and trialkylammonium tetrafluoroborates, such as iPr2NHEtBF4. Constant current electrolysis of
1,3,5-trimethoxybenzene or indoles in DMA containing 0.1 M iPr2NHEtBF4 using an undivided cell equipped with a Pt plate cathode and a Pt wire anode (a quasi-dividedcell) resulted in selective formation of N-acyliminium ions of DMA at the anode, which reacted with arenes to give the corresponding
amidomethylated products in good to high yields.
Keywords: electrochemical oxidation; Friedel–Crafts type amidomethylation; N-acyliminium ion; quasi-dividedcell; trialkylammonium salt; Introduction
Oxidation of amides generates useful intermediates, N-acyliminium ions, which have been widely used in organic
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Graphical Abstract
Scheme 1:
Generation of N-acyliminium ion: previous and present works.