Issue 1, 2024

Oxidative cleavage of ketoximes to ketones using photoexcited nitroarenes

Abstract

The methoxime group has emerged as a versatile directing group for a variety of C–H functionalizations. Despite its importance as a powerful functional handle, conversion of methoximes to the parent ketone, which is often desired, usually requires harsh and functional group intolerant reaction conditions. Therefore, the application of methoximes and their subsequent conversion to the corresponding ketone in a late-stage context can be problematic. Here, we present an alternative set of conditions to achieve mild and functional group tolerant conversion of methoximes to the parent ketones using photoexcited nitroarenes. The utility of this methodology is showcased in its application in the total synthesis of cephanolide D. Furthermore, mechanistic insight into this transformation obtained using isotope labeling studies as well as the analysis of reaction byproducts is provided.

Graphical abstract: Oxidative cleavage of ketoximes to ketones using photoexcited nitroarenes

Supplementary files

Article information

Article type
Edge Article
Submitted
12 Oct 2023
Accepted
17 Nov 2023
First published
24 Nov 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 213-219

Oxidative cleavage of ketoximes to ketones using photoexcited nitroarenes

L. T. Göttemann, S. Wiesler and R. Sarpong, Chem. Sci., 2024, 15, 213 DOI: 10.1039/D3SC05414D

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