Friedel–Crafts Reaction of Arenes by Oxidatively Generated Metal Carbene: Divergent Synthesis of Polycyclic Aromatic Hydrocarbons via Controllable Cyclization of Ynones
Abstract
The Friedel–Crafts reaction of arenes by oxidatively generated α-oxo copper carbenes is disclosed for the first time, in which easily available ynones are transformed in one pot into polycyclic aromatic hydrocarbons through sequential oxidative copper catalysis and base-promoted cyclization, which is complementary to the traditional generation of copper carbenes from diazo compounds. Importantly, the replacement of traditional diazo substrates with ynones allows a safe and convenient procedure for the generation of copper carbenes. In addition, when the same ynones are employed as starting materials, benzoylbenzo[ a ]azulen-10(9a H )-ones bearing synthetically challenging quaternary carbons can be exclusively formed under gold catalysis.
Fields of Study & Subjects
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Cyclopropane Reaction Mechanisms
Organic and Inorganic Chemical Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 23
- Pages
- 7078–7083
- Publication date
- 6 May 2026
- Language
- EN