Electro-mechanochemical approach towards the chloro sulfoximidations of allenes under solvent-free conditions in a ball mill

Abstract

An electro-mechanochemical protocol for the synthesis of vinylic sulfoximines has been developed. Utilising mechanochemically strained BaTiO₃ nanoparticles, the catalytic active system is generated in situ by the reduction of copper(II) chloride. Various combinations of electron-donating and -withdrawing groups are tolerated, and the approach leads to products with difunctionalised double bonds in good to excellent yields. Attempts to add a sulfoximidoyl chloride to an alkyne proved difficult. Additions of a sulfonyl iodide to allenes and alkynes proceeded smoothly in the presence of silica gel without the need for activation by a piezoelectric material.