Work

Visible-light-induced cascade radical cyclization of aryl alkynoates with fluoroalkyl carboxylic anhydrides to construct fluoroalkylated coumarins

Year: 2025

Type: article

Abstract: We herein described an efficient and practical protocol for radical cyclization of aryl alkynoates to access 3-fluoroalkyl-substituted coumarins using readily available, easy-to-handle and low-cost fluoroalkyl carboxylic anhydride as fluoroalkyl source. This method is featured by its generally applicable to several kinds of fluoroalkyl carboxylic anhydrides including difluoromethy1, trifluoromethyl, pentafluoroethyl, heptafluoropropyl and chlorodifluoromethyl, as well as a good functional group tolerance with respect to a wide variety of aryl alkynoates. This reaction was triggered by addition of fluoroalkyl radical to the triple bond of alkynoates, followed by a cascade 5- exo cyclization/oxidization/1,2-ester migration/rearomatization process.

Source: Green Synthesis and Catalysis

DOI: 10.1016/j.gresc.2025.05.007