Acrolein triftosylhydrazone: a versatile vinylcarbene reagent

Abstract

We report the development of acrolein triftosylhydrazone (AHZ-Tfs), an operationally simple allylation reagent serving as an efficient in situ source of highly unstable vinyldiazomethane. This reagent enables catalytic reactions of unsubstituted vinylcarbene, such as Doyle–Kirmse reaction, cyclopropanation, and Si–H insertion, producing access to allyl-containing compounds with outcomes superior to those obtained using pre-prepared vinyl diazomethane.