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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 154-159 |
| Number of pages | 6 |
| Journal | Chemical Science |
| Volume | 15 |
| Issue number | 1 |
| DOIs | |
| State | Published - Nov 25 2023 |
Funding
We thank the National Institute of General Medical Sciences (R35 GM136440) and Northwestern University for financial support of this work. We thank Dr Qiupeng Peng (NU) for help with HRMS. We thank Meemie Hwang (NU) for assistance with FT-IR and Cullen R. Schull (NU) for assistance with the manuscript.
ASJC Scopus subject areas
- General Chemistry