Design of efficient ketone catalysts for epoxidation by using the field effect

By using the field effect (through-space charge-dipole or dipole-dipole int eractions), efficient ketone catalysts 7 and 10 were developed for in situ epoxidation of olefins with Oxone. With either ketone 7 (10-20 mol %) or 10 (5-10 mol %) as catalyst, epoxidation of various olefins (2 mmol scale) at room temperature with 1.5 equiv of Oxone was complete in a short period of time with excellent isolated yields of epoxides (80-97%) and good ketone r ecovery (similar to 80%). Furthermore, the in situ epoxidation of olefins c an be performed on a large scale (20-100 mmol) directly with 5 mol % of com mercially available tetrahydrothiopyran-4-one, which is oxidized by Oxone t o ketone 10 during the epoxidation reactions.