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DOI: 10.1055/s-0041-1737490
Continuous Flow Microreactor Promoted the Catalytic N-Oxidation Reaction of Pyridine Derivatives
This research was supported by the Chinese Academy of Sciences, ‘Light of West China’ Program and PetroChina Innovation Foundation.
Abstract
A simple continuous flow microreactor was successfully constructed for the N-oxidation of pyridine. The continuous flow microreactor used titanium silicalite (TS-1) in a packed-bed microreactor and H2O2 (in methanol as solvent) as the catalytic oxidation system for the formation of various pyridine N-oxides in up to 99% yields. This process is a safer, greener, and more highly efficiency process than using a batch reactor. The device was used for over 800 hours of continuous operation with the catalyst maintaining great activity thus providing great potential for large-scale production.
Key words
continuous flow microreactor - hydrogen peroxide - N-oxidation - pyridine - green synthesis - titanium silicaliteSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737490.
- Supporting Information
Publication History
Received: 16 March 2022
Accepted after revision: 26 April 2022
Article published online:
02 June 2022
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References
- 1 Li D, Wu P, Sun N, Lu Y.-J, Wong W.-L, Fang Z, Zhang K. Curr. Org. Chem. 2019; 23: 616
- 2a Tan Y, Barrios-Landeros F, Hartwig JF. J. Am. Chem. Soc. 2012; 134: 3683
- 2b Talbot EP. A, Richardson M, McKenna JM, Toste FD. Adv. Synth. Catal. 2014; 356: 687
- 2c Jones DH, Kay ST, McLellan JA, Kennedy AR, Tomkinson NC. O. Org. Lett. 2017; 19: 3512
- 2d Zhong J, Long Y, Yan X, He S, Ye R, Xiang H, Zhou X. Org. Lett. 2019; 21: 9790
- 2e Jiao L.-Y, Yin X.-M, Liu S, Zhang Z, Sun M, Ma X.-X. Catal. Commun. 2020; 135: 105889
- 3a Wang K.-B, Ran R.-Q, Xiu S.-D, Li C.-Y. Org. Lett. 2013; 15: 2374
- 3b Harris RJ, Widenhoefer RA. Angew. Chem. Int. Ed. 2014; 53: 9369
- 3c Okugawa Y, Hirano K, Miura M. Angew. Chem. Int. Ed. 2016; 55: 13558
- 3d Beatty JW, Douglas JJ, Miller R, McAtee RC, Cole KP, Stephenson CR. J. Chem 2016; 1: 456
- 4a Beyeh NK, Puttreddy R. Dalton Trans. 2015; 44: 9881
- 4b Ouizem S, Rosario-Amorin D, Dickie DA, Hay BP, Paine RT. Polyhedron 2015; 101: 37
- 4c Ishihara K, Lu Y. Chem. Sci. 2016; 7: 1276
- 4d Lynch W, Lynch G, Sheriff K, Padgett C. Acta Crystallogr., Sect. E 2018; 74: 1405
- 5a Zhou L, Zhang M, Li W, Zhang J. Angew. Chem. Int. Ed. 2014; 53: 6542
- 5b Yoshida K, Takao K.-i. Tetrahedron Lett. 2014; 55: 6861
- 5c Fukumoto Y, Okazaki N, Chatani N. Org. Lett. 2019; 21: 1760
- 6a Balzarini J, Stevens M, De Clercq E, Schols D, Pannecouque C. J. Antimicrob. Chemother. 2005; 55: 135
- 6b Stevens M, Pannecouque C, De Clercq E, Balzarini J. Biochem. Pharmacol. 2006; 71: 1122
- 6c Gerisch M, Hafner F.-T, Lang D, Radtke M, Diefenbach K, Cleton A, Lettieri J. Cancer Chemother. Pharmacol. 2018; 81: 195
- 6d Kaieda A, Takahashi M, Takai T, Goto M, Miyazaki T, Hori Y, Unno S, Kawamoto T, Tanaka T, Itono S, Takagi T, Hamada T, Shirasaki M, Okada K, Snell G, Bragstad K, Sang B.-C. Bioorg. Med. Chem. 2018; 26: 647
- 7a Raja V, Sharma AK, Narasimha Rao VV. R. Mater. Lett. 2004; 58: 3242
- 7b Chen M, Han S, Jiang L, Zhou S, Jiang F, Xu Z, Liang J, Zhang S. Chem. Commun. 2010; 46: 3932
- 7c Chi X, Zhang H, Vargas-Zúñiga GI, Peters GM, Sessler JL. J. Am. Chem. Soc. 2016; 138: 5829
- 7d Stross AE, Iadevaia G, Hunter CA. Chem. Sci. 2016; 7: 5686
- 7e Hu L, Lin X.-M, Mo J.-T, Gan H.-L, Yang X.-L, Cai Y.-P. Inorg. Chem. 2017; 56: 4289
- 8a Kress T. J. Org. Chem. 1985; 50: 3073
- 8b Brougham P, Cooper MS, Cummerson DA, Heaney H, Thomson N. Synthesis 1987; 1015
- 8c Zhang H, Huang C.-H. Environ. Sci. Technol. 2005; 39: 593
- 8d Zhu X, Kreutter KD, Hu H, Player MR, Gaul MD. Tetrahedron Lett. 2008; 49: 832
- 9a Mosher HS, Turner L, Carlsmith A. Org. Synth. 1953; 33: 79
- 9b Bockelhe V, Linn WJ. J. Am. Chem. Soc. 1954; 76: 1286
- 9c Ritter H, Licht HH. J. Heterocycl. Chem. 1995; 32: 585
- 9d Hollins RA, Merwin LH, Nissan RA, Wilson WS. J. Heterocycl. Chem. 1996; 33: 895
- 10a Copéret C, Adolfsson H, Khuong TV, Yudin AK, Sharpless KB. J. Org. Chem. 1998; 63: 1740
- 10b Neimann K, Neumann R. Chem. Commun. 2001; 487
- 10c Robinson DJ, McMorn P, Bethell D, Bulman-Page PC, Sly C, King F, Hancock FE, Hutchings GJ. Catal. Lett. 2001; 72: 233
- 10d Rout L, Punniyamurthy T. Adv. Synth. Catal. 2005; 347: 1958
- 10e Xie W, Zheng Y, Zhao S, Yang J, Liu Y, Wu P. Catal. Today 2010; 157: 114
- 10f Zhao W, Yang C. New J. Chem. 2013; 37: 1867
- 10g Yang F, Zhang X, Li F, Wang Z, Wang L. Green Chem. 2016; 18: 3518
- 11a Chen KY, Lin CM, Shu CM, Kao CS. J. Therm. Anal. Calorim. 2006; 85: 87
- 11b Kertalli E, van Rijnsoever LS, Paunovic V, Neira d’Angelo MF, Schouten JC, Nijhuis TA. Chem. Eng. Sci. 2016; 165: 36
- 11c Fukuzumi S, Lee Y.-M, Nam W. Chin. J. Catal. 2021; 42: 1241
- 11d Targhan H, Evans P, Bahrami K. J. Ind. Eng. Chem. 2021; 104: 295
- 12a Jähnisch K, Hessel V, Löwe H, Baerns M. Angew. Chem. Int. Ed. 2004; 43: 406
- 12b Kiwi-Minsker L, Renken A. Catal. Today 2005; 110: 2
- 12c Gascon J, van Ommen JR, Moulijn JA, Kapteijn F. Catal. Sci. Technol. 2015; 5: 807
- 12d Ötvös SB, Kappe OC. Green Chem. 2021; 23: 6117
- 12e Fu WC, MacQueen PM, Jamison TF. Chem. Soc. Rev. 2021; 50: 7378
- 13 Klassen NV, Marchlngton D, McGowan HC. E. Anal. Chem. 1994; 66: 2921
- 14 Wang Y, Li H, Liu W, Lin Y, Han X, Wang Z. Trans. Tianjin Univ. 2018; 24: 25
The application of pyridine N-oxides in organic intermediates:
The application of pyridine N-oxides in oxidants:
The application of pyridine N-oxides in ligands:
The application of pyridine N-oxides in catalysts:
The application of pyridine N-oxides in drugs:
The application of pyridine N-oxides in materials:
The preparation of pyridine N-oxides with strong oxidants:
The preparation of pyridine N-oxides with H2O2 in acetic acid:
Catalytic methods for the N-oxidation reaction of pyridine:
The risk for the utilization of H2O2 in batch reaction:
Selected reviews for continuous flow microreaction: