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Oxidation of benzylic alcohols to carbonyls using N heterocyclic stabilized λ3-iodanes

26 February 2024, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We introduce N heterocycle-stabilized iodanes (NHIs) as suitable reagents for the mild oxidation of activated alcohols. Two different protocols, both involving activation by chloride additives, were used to synthesize benzylic ketones and aldehydes without overoxidation in up to 97% yield. Based on MS-experiments an activated hydroxy(chloro)iodane is proposed as the reactive intermediate.

Keywords

hypervalent iodine
oxidation
iodanes
alcohols

Supplementary materials

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Experimental details and spectroscopic data.
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Version History

Feb 26, 2024 Version 1

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The content is available under CC BY NC 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2024-t3b6h
D O I: 10.26434/chemrxiv-2024-t3b6h [opens in a new tab]

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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