Pd-catalyzed siloxycyclopropanation of alkenes

Abstract

Unlike electron-deficient and electronically neutral carbenes, alkoxycarbenes, a class of electron-rich carbenes, cannot be used in metal-catalyzed cyclopropanation reactions due to the instability of the corresponding carbene precursors (i.e., diazoalkanes). Although siloxycarbenes can be generated from acylsilanes under photoirradiation or heating at a temperature above 250°C, except for electron-deficient alkenes, the resulting electron-rich carbenes do not react with alkenes.