Beilstein J. Org. Chem.2023,19, 771–777, doi:10.3762/bjoc.19.57
single electron transfer (SET), is proposed to be involved in the plausible reaction mechanism.
Keywords: arylsulfonylimine; benzylic oxidation; benzyl sulfonamide; K2S2O8; sulfate radical anion; Introduction
Among various imine compounds [1], N-arylsulfonylimines are perhaps the most prominent due to
-arylsulfonylimine 2, generated in situ from the corresponding N-(arylsulfonyl)benzylamine 1, undergoes transimination with the ortho-substituted aniline 3 to form imine 3ab via 3aa. Subsequent intramolecular nucleophilic addition in imine 3ab produces intermediate 3ac, which upon oxidation delivers the desired N
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Graphical Abstract
Scheme 1:
Various synthetic approaches to N-arylsulfonylimines.