Effective fluoroalkylation of aldehydes by σ-perfluoroalkyl-iron compounds

Abstract

Organoiron compounds with σ-perfluoroalkyl-iron bonds are well-known and common compounds convenient to prepare and handle. However, their application in organic synthesis was restricted to the introduction of fluoroalkyl group only into electron rich organic molecules such as arenes and thiols [I.I. Gerus, Yu.L. Yagupolskii and L.M. Yagupolskii, J. Org. Chem. (Russ. ed.), 21 (1985) 1852; C.G. Krespan, J. Fluor. Chem., 40 (1988) 129]. In this work we have succeeded in the use of the perfluoroalkyltetracarbonyliron iodides for the nucleophilic fluoroalkylation of aldehydes: ▪ The reaction is rapid (∼ 1 h), easy to carry out and does not require an inert atmosphere. From the synthetic point of view it is promising since the starting organoiron compounds are readily prepared from fluoroalkyl iodides and solid substances stable in air.