Photoinduced cerium-catalyzed C-H acylation of unactivated alkanes

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. Ketones are ubiquitous motifs in the realm of pharmaceuticals and natural products.

Automated summary

In this study, a cerium-catalyzed acylation reaction was reported, which can acylate unactivated C(sp3)-H bonds under mild and operationally-friendly conditions. The reaction shows excellent generality, accommodating a wide range of feedstock chemicals, and facilitating the late-stage functionalization of pharmaceuticals.