Photocatalyzed Synthesis of 3‐Substituted Phthalides: A Key Access to (±)‐Herbaric Acid. Issue 4 (4th January 2023)

• Record Type: Journal Article
• Authors: Fortier, Lucas; Gosset, Cyrille; Lefebvre, Corentin; Pellegrini, Sylvain; Pélinski, Lydie; Bousquet, Till
• Is Part Of: European journal of organic chemistry. Volume 26:Issue 4(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-01-04
• Subjects: oxa-Michael cyclization -- phthalides, photocatalysis -- 4-CzIPN -- (±)-herbaric acid; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202201247
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: An efficient organophotocatalyzed protocol was developed for the preparation of 3‐substituted phthalides. The presented transformation was performed under particularly mild conditions within 6 h and was ultimately applied to a precursor of the herbaric acid. Abstract : Herein, we investigated a new organophotocatalyzed protocol enabling the preparation of 3‐substituted phthalides. From this work, the 1, 2, 3, 5‐Tetrakis(carbazol‐9‐yl)‐4, 6‐dicyanobenzene (4CzIPN) turned out to be a particularly efficient organophotocatalyst to promote lactone formation under visible‐light irradiation within 6 h. Ultimately, it was found that this protocol could enable the formation of racemic herbaric acid.