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Copper catalysed oxidative α-sulfonylation of branched aldehydes using the acid enhanced reactivity of manganese(iv) oxide

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Abstract

The oxidative coupling of secondary aldehydes and sulfinate salts is achieved using copper catalysis to form α-sulfonyl aldehydes. The use of an acidic co-solvent is important to adjust the oxidation potential of MnO2 as an oxidant. A broad range of sulfonylated aldehydes is prepared, and their further functionalisation is demonstrated. A dual ionic/radical pathway mechanism is proposed.

Graphical abstract: Copper catalysed oxidative α-sulfonylation of branched aldehydes using the acid enhanced reactivity of manganese(iv) oxide

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Article information


Submitted
28 Feb 2020
Accepted
17 Mar 2020
First published
17 Mar 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Copper catalysed oxidative α-sulfonylation of branched aldehydes using the acid enhanced reactivity of manganese(IV) oxide

J. I. Higham and J. A. Bull, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC01576H

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