One-pot oxidative amidation of aldehydes via the generation of nitrile imine intermediates

Henry, Martyn C. and Minty, Laura and Kwok, Alexander C. W. and Elwood, Jessica M. L. and Foulis, Adam J. and Pettinger, Jonathan and Jamieson, Craig (2024) One-pot oxidative amidation of aldehydes via the generation of nitrile imine intermediates. Journal of Organic Chemistry. ISSN 0022-3263 (https://doi.org/10.1021/acs.joc.4c00575)

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Abstract

A one-pot procedure for the oxidative amidation of aldehydes via the in situ generation of reactive nitrile imine (NI) intermediates has been developed. Distinct from our progenitor processes, mechanistic and control experiments revealed that the NI undergoes rapid oxidation to an acyl diazene species, which then facilitates N-acylation of an amine. A range of substrates have been explored, including application in the synthesis of pharmaceutically relevant compounds.

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