Mechanistic study of pyrazole synthesis via oxidation-induced N-N coupling of diazatitanacycles

Yukun Cheng; Daniel N. Huh; Ian A. Tonks

doi:10.1039/d4dt01412j

Mechanistic study of pyrazole synthesis via oxidation-induced N-N coupling of diazatitanacycles

Yukun Cheng, Daniel N. Huh, Ian A. Tonks

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Abstract

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.

Original language	English (US)
Pages (from-to)	9510-9515
Number of pages	6
Journal	Dalton Transactions
Volume	53
Issue number	22
DOIs	https://doi.org/10.1039/d4dt01412j
State	Published - May 15 2024
Externally published	Yes

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© 2024 The Royal Society of Chemistry.

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abstract = "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.",

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AU - Tonks, Ian A.

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N2 - 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.

AB - 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.

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Mechanistic study of pyrazole synthesis via oxidation-induced N-N coupling of diazatitanacycles

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