UC Santa Barbara

The 1,3-dipolar cycloadditions of nitrile oxides onto alkenes or alkynes, which afford isoxazolines or isoxazoles, respectively, suffer from errant reactivity profile due to unstable intermediates, harsh reaction conditions, and environmentally irresponsible solvents. Aldoximes can be converted into the highly reactive, non-isolable nitrile oxides by oxidation with hypervalent iodine(III) reagents; however, they have similarly been restricted to use in traditional organic media. An operationally simple and mild method catalytic in hypervalent iodine has been developed that leverages aqueous micellar media derived from TPGS-750-M media that enables efficient, controlled nitrile oxide cycloadditions under mild conditions.