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Abstract | Cited by

Metal-mediated inner-sphere N–N coupling is an uncommon route to N–N bond formation. Herein, we report a mechanistic study of pyrazole formation via oxidation-induced N–N coupling of diazatitanacycles. In TEMPO oxidation reactions, the first of two oxidations is rate limiting and TEMPO coordination to Ti is critical for reactivity. In oxidations with Fc+ salts, coordinating counteranions such (eg. Cl−) aid an “inner-sphere-like” oxidation.

Graphical abstract: Mechanistic study of pyrazole synthesis via oxidation-induced N–N coupling of diazatitanacycles

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