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

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