Tandem α-Arylation/Cyclization of 4-Haloacetoacetates with Arynes: A Metal-Free Approach toward 4-Aryl-3-(2 H)-furanones

J Org Chem. 2019 May 3;84(9):5957-5964. doi: 10.1021/acs.joc.9b00488. Epub 2019 Apr 16.

Abstract

An efficacious, metal-free strategy has been developed for the synthesis of 4-aryl-3-(2 H)-furanones. The reaction proceeds via the nucleophilic addition of an active methylene compound to the aryne followed by ring closing of the adduct. The reaction proceeds under mild conditions, is applicable for gram-scale synthesis of 4-aryl-3-(2 H)-furanones, and is general for a range of substituted arynes and haloacetates.