Metal-free synthesis of 1,1-dimethyl-2,2,2-trifluoroethyl substituted quinazolinones via tandem radical cyclization of quinazolin-4(3H)-ones with 3,3,3-trifluoro-2,2-dimethylpropanoic acid.

Abstract

A metal-free (NH4)2S2O8-mediated decarboxylative trifluoromethylation reaction of alkenes with 3,3,3-trifluoro-2,2-dimethylpropionic acid has been proposed. This method offers a novel route for the direct synthesis of a series of CMe2CF3-containing quinazolinones from basic chemical raw materials. The reaction mechanism was studied by a radical trapping test and DFT methods, verifying an oxidation-triggered cascade process promoted by the CMe2CF3 radicals. This strategy provides advantages such as high yield, wide substrate compatibility, and high atom economy.