Issue 1, 2024

Photoinduced cerium-catalyzed C–H acylation of unactivated alkanes

Abstract

Ketones are ubiquitous motifs in the realm of pharmaceuticals and natural products. Traditional approaches to accessing these species involve the addition of metal reagents to carboxyl compounds under harsh conditions. Herein, we report a cerium-catalyzed acylation of unactivated C(sp3)–H bonds using bench-stable acyl azolium reagents under mild and operationally-friendly conditions. This reaction exhibits excellent generality, accommodating a wide range of feedstock chemicals such as cycloalkanes and acyclic compounds as well as facilitating the late-stage functionalization of pharmaceuticals. We demonstrate further applications of our strategy with a three-component radical relay reaction and an enantioselective N-heterocyclic carbene (NHC) and cerium dual-catalyzed reaction.

Graphical abstract: Photoinduced cerium-catalyzed C–H acylation of unactivated alkanes

Supplementary files

Article information

Article type
Edge Article
Submitted
29 sen 2023
Accepted
09 noy 2023
First published
25 noy 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, 154-159

Photoinduced cerium-catalyzed C–H acylation of unactivated alkanes

J. Cao, J. L. Zhu and K. A. Scheidt, Chem. Sci., 2024, 15, 154 DOI: 10.1039/D3SC05162E

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