Selectfluor-Mediated Oxidative Dehydrogenation of Hydrazines: A Process for the Synthesis of Azo Compounds

Yulei Zhao; Shuai Li; Jinjie Cui; Huimin Wang; Xin Kang; Yan Wang; Laijin Tian

doi:10.1055/a-1899-5563

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(23): 5245-5252
DOI: 10.1055/a-1899-5563

paper

Selectfluor-Mediated Oxidative Dehydrogenation of Hydrazines: A Process for the Synthesis of Azo Compounds

Yulei Zhao ∗

^aShandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China

,

Shuai Li‡

^aShandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China

,

Jinjie Cui

^aShandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China

,

Huimin Wang

^aShandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China

,

Xin Kang

^aShandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China

,

Yan Wang

^bHospital of University, Qufu Normal University, Qufu 273165, P. R. of China

,

Laijin Tian

^aShandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China

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Abstract

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Abstract

A facile method to synthesize azo compounds from hydrazine derivatives is developed. This represents the unprecedented example of Selectfluor-mediated oxidative dehydrogenation of hydrazine derivatives. The reaction might proceed through N-fluorination and elimination processes. This protocol exhibits key features including simple operation, mild conditions, good functional group tolerance, and high efficiency. Moreover, the advantage is also highlighted by the conversion of a sulfonyl-substituted azo compound to furnish acetanilide in excellent yield under 4 W blue LED irradiation.

Key words

oxidation - dehydrogenation - azo compounds - hydrazines - Selectfluor

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Referenzen

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