Visible Light-Induced Metal-free Arylation of Coumarin-3-carboxylates with Arylboronic Acids.

Abstract

The present work represents a novel methodology for the selective arylation of coumarin-3-carboxylates with arylboronic acids via a photochemical route, marking the first-ever attempt for the direct alkenyl C-H arylation using rose bengal as a photocatalyst, which is a readily available and cost-effective alternative to transition metal catalysis. The reaction proceeds smoothly in MeOH/H2O solvent media in the presence of radical initiator affording the arylated products in good yields (60-80 %). The reaction parameters such as visible light, radical initiator, oxidant, anhydrous solvent, and inert atmosphere play a crucial role for the success of this methodology. The substituents present on the substrate show a significant effect on the conversion. This study provides a valuable contribution to the field of organic synthesis offering a new and efficient approach to the arylation of coumarin-3-carboxylic acid esters with a broad substrate scope and high functional group tolerance. It is a versatile method and provides a direct access to biologically relevant 4-arylcoumarin-3-carboxylates.