An umpolung strategy allowing the use of stilbenes as electrophiles in substitution reactions is developed that relies on a combination of m-chloroperbenzoic acid and hexafluoroisopropanol. This new step-economic approach gives rise to benzhydryl derivatives by the use of different nitrogenated, oxygenated, and sulfur- and carbon-based nucleophiles.

Benzhydryl derivatives are synthesized by a new strategy involving the use of stilbenes as an electrophilic reaction partner through umpolung reactivity in a nucleophilic substitution reaction. The transformation, which requires oxidative treatment with meta-chloroperoxybenzoic acid and the presence of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as an essential solvent and reaction promoter, occurs through multiple consecutive steps. Under these conditions, different benzhydryl derivatives are synthesized by coupling stilbenes with a variety of nitrogenated, oxygenated, and sulfur- and carbon-based nucleophiles.