Co(OAc)2/TBHP as a Highly Active Catalytic System for the Selective Oxidation of Aromatic Amines to Nitro Derivatives

Liqiong Wu; Lifeng Yao; Weiyan Yin; Junxia Yu

doi:10.1055/a-2110-8622

Synthesis, Table of Contents

Synthesis 2023; 55(19): 3104-3108
DOI: 10.1055/a-2110-8622

paper

Co(OAc)₂/TBHP as a Highly Active Catalytic System for the Selective Oxidation of Aromatic Amines to Nitro Derivatives

Authors

Liqiong Wu

^aSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430074, P. R. of China

^bHubei Key Laboratory of Biomass Fibers and Eco-dyeing & Finishing, School of Chemistry and Chemical Engineering, Wuhan Textile University, Wuhan 430073, P. R. of China
Lifeng Yao

^cSchool of Chemistry and Chemical Engineering, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China
Weiyan Yin∗

^aSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430074, P. R. of China

^bHubei Key Laboratory of Biomass Fibers and Eco-dyeing & Finishing, School of Chemistry and Chemical Engineering, Wuhan Textile University, Wuhan 430073, P. R. of China

^dState Environmental Protection Key Laboratory of Mineral Metallurgical Resources Utilization and Pollution Control, Wuhan University of Science and Technology, Wuhan 430081, P. R. of China
Junxia Yu∗

^aSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430074, P. R. of China

Abstract

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Abstract

An efficient cobalt-catalyzed protocol for the selective oxidation of anilines using a combination of inexpensive tert-butyl hydroperoxide and Co(OAc)₂·4H₂O without any ligand has been developed, providing the nitroarene products in good to excellent yields (up to 96%).

Key words

Co(OAc)₂·4H₂O - tert-butyl hydroperoxide - ligand-free - selective oxidation - aromatic amines

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References

References
1 Ju KS, Parales RE. Microbiol. Mol. Biol. Rev. 2010; 74: 250
2 Tetreault S, Ananthanarayanan VS. J. Med. Chem. 1993; 36: 1017
3 Kulkarni AA. Beilstein J. Org. Chem. 2014; 10: 405
4 Fan FR. F, Yao Y, Cai L, Cheng L, Tour JM, Bard AJ. J. Am. Chem. Soc. 2004; 126: 4035
5 Singh A, Kociok-Köhn G, Trivedi M, Chauhan R, Kumar A, Gosavi SW, Terashima C, Fujishima A. New J. Chem. 2019; 43: 4745
6 Ippen H. Int. Arch. Occup. Environ. Health. 1994; 66: 283
7 Qin C, Dang M, Meng Y, Zhao D. Process Saf. Prog. 2022; 42: 21
8 Ravi K, Bankar BD, Jindani S, Biradar AV. ACS Omega. 2019; 4: 9453
9 Maiorana S, Baldoli C, Licandro E, Casiraghi L, Magistris ED, Paio A, Provera S, Seneci P. Tetrahedron Lett. 2000; 41: 7271
10 Chuang HY, Schupp M, Meyrelles R, Maryasin B, Maulide N. Angew. Chem. Int. Ed. 2021; 60: 13778
11 Emmons WD. J. Am. Chem. Soc. 1957; 79: 5528
12 Huang B, Fan C, Yu H, Ma J, Pan C, Zhang D, Zheng A, Li Y, Sun Y. Mol. Catal. 2018; 446: 140
13 Meenakshi R, Shakeela K, Kutti Rani S, Ranga Rao G. Catal. Lett. 2017; 148: 246
14 Murray RW, Jeyaraman R, Mohan L. Tetrahedron Lett. 1986; 27: 2335
15 China H, Tanihara K, Sasa H, Kikushima K, Dohi T. Catal. Today 2020; 348: 2
16 Sun Y, Liu H, Tan X, Li Z, Du Y, Zheng A, Liu X, Peng N. RSC Adv. 2019; 9: 1889
17 Ratnikov MO, Farkas LE, McLaughlin EC, Chiou G, Choi H, el-Khalafy SH, Doyle MP. J. Org. Chem. 2011; 76: 2585
18 Jayachandran B, Sasidharan M, Sudalai A, Ravindranathan T. J. Chem. Soc., Chem. Commun. 1995; 1523
19 Reddy KR, Maheswari CU, Venkateshwar M, Kantam ML. Adv. Synth. Catal. 2009; 351: 93
20 Wu S, Wei K, Fang W. ChemistrySelect 2021; 6: 234
21 Lin W, Cao E, Zhang L, Xu X, Song Y, Liang W, Sun M. Nanoscale 2018; 10: 5482
22 Daikopoulou V, Skliri E, Koutsouroubi ED, Armatas GS, Lykakis IN. ChemPlusChem 2021; 87: e202100413
23 Zoubi Al W, Ko YG. J. Organomet. Chem. 2016; 822: 173
24 Okunola-Bakare OM, Cao J, Kopajtic T, Katz JL, Loland CJ, Shi L, Newman AH. J. Med. Chem. 2014; 57: 1000

Supplementary Material

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