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Mupparapu N.,Indian Institute of Integrative Medicine | Mupparapu N.,Academey of Scientific and Innovative Research | Battini N.,Indian Institute of Integrative Medicine | Battini N.,Academey of Scientific and Innovative Research | And 8 more authors.
Chemistry - A European Journal | Year: 2015

Given the attractive ability of iminium ions to functionalize molecules directly at ostensibly unreactive positions, the reactivity of iminium ions, in which an α CH2 group is replaced by C=O was explored. Background studies on the ability of such iminium cations to promote reactions via an iminium-catalyzed or iminium-equivalent pathway are apparently unavailable. Previously, tandem cross-coupling reactions were reported, in which an iminium ion undergoes nucleophilic 1,2-addition to give a putative three-component intermediate that abstracts a proton in situ and undergoes self-deamination followed by unprecedented DMSO/ aerobic oxidation to generate a-ketoamides. However, later it was observed that iminium ions can generate valuable α-ketoamides through simple aerobic oxidation. In all reactions, iminium ions were generated in situ by reaction of 2-oxoaldehydes with secondary amines. © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Source

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