Oxidative Dehydrogenation of Hydrazobenzenes Toward Azo Compounds Catalyzed by -Butyl Nitrite in EtOH

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2020 Nov 16

PMID 33195938

Citations 3

Authors

Zhi-Qiang Wang

Jiang-Xi Yu

Shan-Qin Bai

Bang Liu

Cheng-Yong Wang

Jin-Heng Li

Affiliations

Soon will be listed here.

Abstract

We describe a -butyl nitrite-catalyzed oxidative dehydrogenation of hydrazobenzenes for producing azobenzenes. This method proceeds at ambient temperature and under an atmospheric environment by employing eco-friendly EtOH as the medium, representing a mild, general route to the synthesis of various symmetrical and nonsymmetrical azobenzenes in excellent yields with broad functional group tolerance.

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References

Zhang C, Jiao N . Copper-catalyzed aerobic oxidative dehydrogenative coupling of anilines leading to aromatic azo compounds using dioxygen as an oxidant. Angew Chem Int Ed Engl. 2010; 49(35):6174-7. DOI: 10.1002/anie.201001651. View

Kim M, Kim J . Aerobic Oxidation of Alkyl 2-Phenylhydrazinecarboxylates Catalyzed by CuCl and DMAP. J Org Chem. 2018; 83(3):1673-1679. DOI: 10.1021/acs.joc.7b03119. View

Hu L, Cao X, Chen L, Zheng J, Lu J, Sun X . Highly efficient synthesis of aromatic azos catalyzed by unsupported ultra-thin Pt nanowires. Chem Commun (Camb). 2012; 48(28):3445-7. DOI: 10.1039/c2cc30281k. View

Feng K, Ban Y, Yuan P, Lei W, Liu Q, Fang R . Synthesis of 4-Oxoisoxazoline N-Oxides via Pd-Catalyzed Cyclization of Propargylic Alcohols with tert-Butyl Nitrite. Org Lett. 2019; 21(9):3131-3135. DOI: 10.1021/acs.orglett.9b00811. View

Chen Y, Ma Y, Li L, Jiang H, Li Z . Nitration-Peroxidation of Alkenes: A Selective Approach to β-Peroxyl Nitroalkanes. Org Lett. 2019; 21(5):1480-1483. DOI: 10.1021/acs.orglett.9b00266. View

Liu Y, Zhang J, Song R, Qian P, Li J . Cascade nitration/cyclization of 1,7-enynes with tBuONO and H2O: one-pot self-assembly of pyrrolo[4,3,2-de]quinolinones. Angew Chem Int Ed Engl. 2014; 53(34):9017-20. DOI: 10.1002/anie.201404192. View

Ning X, Wang M, Yao C, Chen X, Kang Y . tert-Butyl Nitrite: Organic Redox Cocatalyst for Aerobic Aldehyde-Selective Wacker-Tsuji Oxidation. Org Lett. 2016; 18(11):2700-3. DOI: 10.1021/acs.orglett.6b01165. View

Takeda Y, Okumura S, Minakata S . Oxidative dimerization of aromatic amines using tBuOI: entry to unsymmetric aromatic azo compounds. Angew Chem Int Ed Engl. 2012; 51(31):7804-8. DOI: 10.1002/anie.201202786. View

Sharma P, Rane N, Gurram V . Synthesis and QSAR studies of pyrimido[4,5-d]pyrimidine-2,5-dione derivatives as potential antimicrobial agents. Bioorg Med Chem Lett. 2004; 14(16):4185-90. DOI: 10.1016/j.bmcl.2004.06.014. View

10.

Grirrane A, Corma A, Garcia H . Gold-catalyzed synthesis of aromatic azo compounds from anilines and nitroaromatics. Science. 2008; 322(5908):1661-4. DOI: 10.1126/science.1166401. View

11.

Chen F, Huang X, Li X, Shen T, Zou M, Jiao N . Dehydrogenative N-incorporation: a direct approach to quinoxaline N-oxides under mild conditions. Angew Chem Int Ed Engl. 2014; 53(39):10495-9. DOI: 10.1002/anie.201406479. View

12.

Kennedy D, Vembu N, Fronczek F, Devocelle M . Synthesis of mutual azo prodrugs of anti-inflammatory agents and peptides facilitated by α-aminoisobutyric acid. J Org Chem. 2011; 76(23):9641-7. DOI: 10.1021/jo201358e. View

13.

Beharry A, Sadovski O, Woolley G . Azobenzene photoswitching without ultraviolet light. J Am Chem Soc. 2011; 133(49):19684-7. DOI: 10.1021/ja209239m. View

14.

Xu H, Liu P, Li Y, Han F . Copper-mediated direct aryl C-H cyanation with azobisisobutyronitrile via a free-radical pathway. Org Lett. 2013; 15(13):3354-7. DOI: 10.1021/ol401404y. View

15.

Wu Y, Jiang S, Song R, Li J . A metal- and oxidizing-reagent-free anodic para-selective amination of anilines with phenothiazines. Chem Commun (Camb). 2019; 55(30):4371-4374. DOI: 10.1039/c9cc01332f. View

16.

Hu M, Song R, Li J . Metal-free radical 5-exo-dig cyclizations of phenol-linked 1,6-enynes for the synthesis of carbonylated benzofurans. Angew Chem Int Ed Engl. 2014; 54(2):608-12. DOI: 10.1002/anie.201408978. View

17.

Luo M, Li Y, Ouyang X, Li J, He D . Electrochemical dehydrogenative cross-coupling of two anilines: facile synthesis of unsymmetrical biaryls. Chem Commun (Camb). 2020; 56(18):2707-2710. DOI: 10.1039/c9cc09879h. View

18.

Puntoriero F, Ceroni P, Balzani V, Bergamini G, Vogtle F . Photoswitchable dendritic hosts: a dendrimer with peripheral azobenzene groups. J Am Chem Soc. 2007; 129(35):10714-9. DOI: 10.1021/ja070636r. View

19.

He K, Zhang T, Zhang S, Sun Z, Zhang Y, Yuan Y . Tunable Functionalization of Saturated C-C and C-H Bonds of N,N'-Diarylpiperazines Enabled by tert-Butyl Nitrite (TBN) and NaNO Systems. Org Lett. 2019; 21(13):5030-5034. DOI: 10.1021/acs.orglett.9b01574. View

20.

DiCesare N, Lakowicz J . New color chemosensors for monosaccharides based on azo dyes. Org Lett. 2001; 3(24):3891-3. PMC: 6937552. DOI: 10.1021/ol016813p. View