Sulfilimines and sulfoximines by reaction of nitriles with perfluoroalkyl sulfoxides

Abstract

The species obtained by activation of perfluoroalkylated sulfoxides with trifluoromethanesulfonic anhydride behaves as highly electrophilic entities. Their reaction with nitriles allows a Ritter-like process leading to the new fluorinated acylsulfilimines 1-21 after hydrolysis. This flexible methodology allows some variation of both the sulfoxide and nitrile components. Derived acylsulfoximines 22-25 or free sulfoximines 26-28 could be selectively obtained, as needed, by further controlled oxidation with the cheap and nontoxic potassium permanganate. This oxidation may be performed either after isolation of the intermediate sulfilimine, or more conveniently in a one-pot process directly from fluorinated sulfoxides. This versatile, solvent and metal free, reaction is thus an opening way through, the synthesis of new ligands or electrophilic trifluoromethylating reagents, © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.