Issue 39, 2017

Oxidative functionalisation of alcohols and aldehydes via the merger of oxoammonium cations and photoredox catalysis

Abstract

We present a new paradigm for nitroxyl-mediated processes via the merger of oxoammonium cation-mediated oxidation with visible-light photoredox catalysis. The integration of these two forms of catalysis has been realised for the oxidative amidation of aldehydes, furnishing N-acylated heterocycles. Extension of this process to the oxidative amidation of alcohols via the intermediacy of an aldehyde was successfully pursued, thus proffering a general oxidation platform. The activated amides synthesised here are excellent synthetic handles for acylation.

Graphical abstract: Oxidative functionalisation of alcohols and aldehydes via the merger of oxoammonium cations and photoredox catalysis

Supplementary files

Article information

Article type
Paper
Submitted
11 Aug 2017
Accepted
08 Sep 2017
First published
08 Sep 2017

Org. Biomol. Chem., 2017,15, 8295-8301

Oxidative functionalisation of alcohols and aldehydes via the merger of oxoammonium cations and photoredox catalysis

J. Nandi, J. M. Ovian, C. B. Kelly and N. E. Leadbeater, Org. Biomol. Chem., 2017, 15, 8295 DOI: 10.1039/C7OB02243C

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