Radical Reaction Using an Organocopper Reagent Derived from Ethyl Bromodifluoroacetate

Abstract

In our previous work, reaction of ethyl bromodifluoroacetate ( 1 ) in the presence of Cu powder with olefins activated by an electron-withdrawing group gave the Michael-type adducts through an anionic intermediate. The same reaction with non-activated olefins was found to give addition products by a radical mechanism. The radical intermediate from α-methylstyrene was stabilized by a benzene ring and gave novel dimerization products. This reaction with 1-decene provided a convenient route to 2,2-difluorododecanoic acid.