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
a   Shandong 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
a   Shandong 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
a   Shandong 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
a   Shandong 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
a   Shandong 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
b   Hospital of University, Qufu Normal University, Qufu 273165, P. R. of China
,
Laijin Tian
a   Shandong 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
› Author Affiliations
We thank the Natural Science Foundation of Shandong Province (ZR2021MB136 and ZR2018BB026), College Students Innovation and Entrepreneurship Training Project of China (202110446051), and the Doctoral Start-Up Scientific Research Foundation of Qufu Normal University.


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.

Supporting Information



Publication History

Received: 09 June 2022

Accepted after revision: 13 July 2022

Accepted Manuscript online:
13 July 2022

Article published online:
01 September 2022

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