Collect. Czech. Chem. Commun. 2002, 67, 1285-1295

Radical Reaction Using an Organocopper Reagent Derived from Ethyl Bromodifluoroacetate

Kazuyuki Sato, Yuko Ogawa, Misato Tamura, Mika Harada, Terumasa Ohara, Masaaki Omote, Akira Ando and Itsumaro Kumadaki*

Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan


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.

Keywords: Radical additions; Radicals; Alkenes; Fluorine; Fluorinated compounds; Ethyl bromodifluoroacetate; Copper powder.

References: 14 live references.