Metal-mediated radical perfluoroalkylation of organic compounds

The incorporation of fluoroalkyl groups, and particularly the trifluoromethyl group, in pharmaceutical molecules has a profound impact on their physical and biological properties, mainly because of the unique metabolic stability, lipophilicity, and electron-withdrawing nature of the fluoroalkyl substituent. The relevance of the CF3-containing substrates provides the driving force for the development of more efficacious and versatile synthetic protocols for these molecules. In this account, the latest radical trifluoromethylation and perfluoroalkylation reactions with the aid of metals of both aliphatic and aromatic compounds will be discussed. The aim of this account is to review the recently emerging literature (2010-present) on perfluoroalkyl-group addition or substitution reactions performed through radical and radical-ion pathways with the intervention of metals or metalorganic species. (C) 2013 Elsevier B.V. All rights reserved.