The readily available α‐diazo‐β‐oxosulfones have been employed, for the first time, in the Wolff cyclocondensation with aromatic amines promoted by 1.5‐fold excess of TiCl4. The reaction was found to be general (as illustrated by 15 product examples) and resulted in moderate yields of medicinally relevant sulfonyl 1,2,3‐triazoles. Excluding the Lewis acid promoter resulted in a clean and high‐yielding formation of α‐sulfonyl acetanilides resulting from the thermal Wolff rearrangement and trapping of the ketene intermediate with an aniline molecule.
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