Synthesis 2020; 52(07): 1103-1112
DOI: 10.1055/s-0039-1690052
paper
© Georg Thieme Verlag Stuttgart · New York

Trichloroisocyanuric Acid Mediated Oxidative Dehydrogenation of Hydrazines­: A Practical Chemical Oxidation To Access Azo Compounds

College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. China   Email: suyp51@nwnu.edu.cn
,
Xuan Liu
,
Jie Yu
,
Guiyan Cao
,
Rong Zhang
,
Yanan Zhao
,
Danfeng Huang
,
Ke-Hu Wang
,
,
› Author Affiliations
We are thankful for financial support from the National Natural Science Foundation of China (Grant No. 21502154, 21961034, 21362033) and the Science and Technology Program of Gansu Province (No. 17JR5RA073).
Further Information

Publication History

Received: 04 November 2019

Accepted after revision: 23 December 2019

Publication Date:
22 January 2020 (online)


Abstract

A highly efficient, metal-free, chemical oxidation of hydrazines has been implemented using environmentally friendly TCCA as oxidant. This benign protocol provides straightforward access to a wide range of azo compounds in THF in excellent yield. Altogether, 35 azo compounds were obtained in this way and scale-up preparations were performed. Additionally, a plausible mechanism was also proposed. Step-economical process, mild reaction conditions, operational simplicity, high reaction efficiency, and easy scale-up highlight the practicality of this methodology.

Supporting Information

 
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