Work

Dual palladium-organophotoredox catalyzed C–H olefination–annulation of aryl carboxylic acids

Year: 2025

Type: article

Abstract: Herein, we report a dual palladium-photoredox mediated tandem C-H olefination-cyclization of aryl carboxylic acids with both terminal and internal alkenes using molecular oxygen as a green oxidant. This method offers a mild and simple route for the synthesis of various isobenzofuranone derivatives. The synthetic utility of the method was demonstrated by late stage functionalization of various carboxylic acid containing drugs. Further derivatizations of the final isobenzofuranones were performed to access other important molecular scaffolds. Mechanistic studies indicated that the final cyclization step involves an oxopalladation-protodemetallation mechanism rather than a simple oxa-Michael addition commonly employed in other methodologies at elevated temperatures.

Source: Organic & Biomolecular Chemistry

DOI: 10.1039/d5ob00275c

Authors: A Anagha Varma, Purushothaman Gopinath

Institution: Indian Institute of Science Education and Research, Tirupati

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Funders: Department of Science and Technology, Ministry of Science and Technology, India, Council of Scientific and Industrial Research, India, Mission on Nano Science and Technology

Award: G3720062075