Copper(I)/Ligand-Catalyzed 5-<i>endo</i> Radical Cyclization–Aromatization of 2,2,2-Trichloroethyl Vinyl Ethers: Synthesis of 2,3-Difunctionalized 4-Chlorofurans

Abstract

Copper(I)/ligand-catalyzed one pot synthesis of highly substituted 2,3-difunctionalized-4-chlorofurans has been reported. The reaction proceeds via a Cu(I)-catalyzed regioselective 5-endo-trig radical cyclization of 2,2,2-trichloroethyl vinyl ethers followed by the base-promoted dehydrochlorination. The success of the kinetically disfavored 5-endo cyclization was attributed to the formation of captodatively stabilized radical intermediate in the cyclization step and relatively high reaction temperature. Synthetic application of this protocol was also demonstrated in the preparation of alkyl and aryl substituted 4-chlorofuranonapthoquinones.