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The Cp*RuCl-based catalyst enables expedient access to a variety of benzofused six-membered azaheterocycles from unprotected o -alkynylanilines and trimethylsilyldiazomethane through an unprecedent tandem carbene/alkyne metathesis/N-H insertion reaction. The transformation takes place under mild reaction conditions (room temperature, &lt;15 min) and with excellent functional group tolerance. The synthetic utility of the final products and a mechanistic rationale are also discussed.

Ruthenium-Catalyzed Tandem Carbene/Alkyne Metathesis/N–H Insertion: Synthesis of Benzofused Six-Membered Azaheterocycles