Work

Copper‐Catalyzed Regioselective Meta C─H Bond Olefination of Anilides

Year: 2025

Type: article

Abstract: Herein, we report a Cu-catalyzed meta-olefination of anilides using alkenyl iodonium salts. The olefination of a panel of pivanilides was achieved using an additive-free copper-based catalytic system under mild reaction conditions (25 examples, up to 60% yield). By favoring a Heck-like four-membered transition state, the approach demonstrated an excellent regioselectivity for the meta C─H functionalization with β-styrenyl and β-alkyl-alkenyl groups using a weakly coordinated directing group (DG). Postfunctionalization reactions were conducted, highlighting both the synthetic interest of the products and the potential atom-efficiency of the process.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.202500992

Authors: Javid Rzayev, Philippe Jubault, Tatiana Besset

Institutions: Centre National de la Recherche Scientifique, École Nationale Supérieure d'Ingénieurs de Caen, Laboratoire COBRA, Université de Rouen Normandie, Institut National des Sciences Appliquées Rouen Normandie

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,640

Funder: Agence Nationale de la Recherche