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

Author:

Banik Swarnayu12,Saikiran Aita1,Permula Prathyusha12,Srivishnu K. S.32,Sridhar B.4,Reddy B. V. Subba1ORCID

Affiliation:

1. Fluoro &Agrochemicals CSIR-Indian Institute of Chemical Technology Hyderabad 500 007 India

2. Academy of Scientific and Innovative Research (AcSIR) Ghaziabad 201002 India

3. Polymers and Functional Materials CSIR-Indian Institute of Chemical Technology Hyderabad 500007 India

4. Laboratory of X-ray Crystallography CSIR-Indian Institute of Chemical Technology Hyderabad 500 007 India

Abstract

AbstractThe 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.

Publisher

Wiley

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