Copper-Promoted Intramolecular Oxidative Dehydrogenation for Synthesizing Dihydroisocoumarins and Isocoumarins

Qiang Zhang; Lin-Yan Zhang; Xian-Ying Shi

doi:10.3390/molecules28176319

Copper-Promoted Intramolecular Oxidative Dehydrogenation for Synthesizing Dihydroisocoumarins and Isocoumarins

Molecules. 2023 Aug 29;28(17):6319. doi: 10.3390/molecules28176319.

Authors

Qiang Zhang¹, Lin-Yan Zhang², Xian-Ying Shi²

Affiliations

¹ Shaanxi Key Laboratory of Catalysis, School of Chemistry and Environmental Science, Shaanxi University of Technology, Hanzhong 723001, China.
² Key Laboratory of Syngas Conversion of Shaanxi Province, Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.

Abstract

Isocoumarins and dihydroisocoumarins are important skeletons with a wide range of biological activities, such as anti-bacterial, anti-allergy, anti-fungal, anti-tumor, and anti-HIV properties. Herein, we demonstrated divergent syntheses of isocoumarins and 3,4-dihydroisocoumarins by intramolecular dehydrogenative cyclization of 2-(3-oxobutyl) benzoic acids. This transformation undergoes Csp³-H bonds and O-H bonds coupling in air using copper salt. The reactions may undergo free radical process.

Keywords: C–O bond coupling; carboxyl-directed; dihydroisocoumarin; isocoumarin.

Grants and funding

This research received no external funding.