Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2019; 30(14): 1703-1707
DOI: 10.1055/s-0037-1612088
DOI: 10.1055/s-0037-1612088
cluster
Organoselenium-Catalyzed Polymerization of Aniline with Hydrogen Peroxide as Oxidant
This work was financially supported by the Nature Science Foundation of Jiangsu Province (BK20181449), the National Natural Science Foundation of China (21673202), the Jiangsu Provincial Six Talent Peaks Project (XCL-090), and the Priority Academic Program Development of Jiangsu Higher Education Institutions.Further Information
Publication History
Received: 27 November 2018
Accepted after revision: 26 December 2018
Publication Date:
05 February 2019 (online)
Published as part of the Cluster Organosulfur and Organoselenium Compounds in Catalysis
Abstract
A convenient method for the synthesis of polyanilines was developed through the organoselenium-catalyzed oxidation of anilines with H2O2. Unlike reported methods, this reaction generates no wastes other than water. These green features make the method much more practical in terms of large-scale preparation. Moreover, it is the first example of an application of organoselenium catalysis techniques in aniline polymerization reactions and might be an important advance in the fields of both organoselenium catalysis and polyanilines.
Key words
selenium catalysis - organoselenium compounds - green chemistry - aniline - polymerization - polyanilineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612088.
- Supporting Information
-
References and Notes
- 1a Casola KK, Gomes MR, Back DF, Zeni G. J. Org. Chem. 2018; 83: 6706
- 1b Jing X, Chen C, Deng X, Zhang X, Wei D, Yu L. Appl. Organomet. Chem. 2018; 32: e4332
- 1c Liu M, Li Y, Yu L, Xu Q, Jiang X. Sci. China: Chem. 2018; 61: 294
- 1d Kodama S, Saeki T, Mihara K, Higashimae S, Kawaguchi S.-i, Sonoda M, Nomoto A, Ogawa A. J. Org. Chem. 2017; 82: 12477
- 1e Tamai T, Yoshikawa M, Higashimae S, Nomoto A, Ogawa A. J. Org. Chem. 2016; 81: 324
- 1f Sancineto L, Mariotti A, Bagnoli L, Marini F, Desantis J, Iraci N, Santi C, Pannecouque C, Tabarrini O. J. Med. Chem. 2015; 58: 9601
- 2a Freudendahl DM, Santoro S, Shahzad SA, Santi C, Wirth T. Angew. Chem. Int. Ed. 2009; 48: 8409
- 2b Santi C, Santoro S, Battistelli B. Curr. Org. Chem. 2010; 14: 2442
- 2c Santoro S, Azeredo JB, Nascimento V, Sancineto L, Braga AL, Santi C. RSC Adv. 2014; 4: 31521
- 2d Breder A, Ortgies S. Tetrahedron Lett. 2015; 56: 2843
- 2e Młochowski J, Wójtowicz-Młochowska H. Molecules 2015; 20: 10205
- 2f Guo R, Liao L, Zhao X. Molecules 2017; 22: 835
- 3a Depken C, Krätzschmar F, Rieger R, Rode K, Breder A. Angew. Chem. Int. Ed. 2018; 57: 2459
- 3b Rode K, Palomba M, Ortgies S, Rieger R, Breder A. Synthesis 2018; 50: 3875
- 3c Luo J, Cao Q, Cao X, Zhao X. Nat. Commun. 2018; 9: 527
- 3d Liu X, Liang Y, Ji J, Luo J, Zhao X. J. Am. Chem. Soc. 2018; 140: 4782
- 3e Guo R, Huang J, Zhao X. ACS Catal. 2018; 8: 926
- 3f Ortgies S, Rieger R, Rode K, Koszinowski K, Kind J, Thiele CM, Rehbein J, Breder A. ACS Catal. 2017; 7: 7578
- 3g Liao L, Guo R, Zhao X. Angew. Chem. Int. Ed. 2017; 56: 3201
- 3h Ortgies S, Depken C, Breder A. Org. Lett. 2016; 18: 2856
- 3i Guo R, Huang J, Huang H, Zhao X. Org. Lett. 2016; 18: 504
- 3j Cresswell AJ, Eey ST.-C, Denmark SE. Nat. Chem. 2015; 7: 146
- 3k Ortgies S, Breder A. Org. Lett. 2015; 17: 2748
- 3l Deng Z, Wei J, Liao L, Huang H, Zhao X. Org. Lett. 2015; 17: 1834
- 3m Chen F, Tan CK, Yeung Y.-Y. J. Am. Chem. Soc. 2013; 135: 1232
- 3n Trenner J, Depken C, Weber T, Breder A. Angew. Chem. Int. Ed. 2013; 52: 8952
- 4a Sancineto L, Tidei C, Bagnoli L, Marini F, Lenardao EJ, Santi C. Molecules 2015; 20: 10496
- 4b Santi C, Di Lorenzo R, Tidei C, Bagnoli L, Wirth T. Tetrahedron 2012; 68: 10530
- 4c Santoro S, Santi C, Sabatini M, Testaferri L, Tiecco M. Adv. Synth. Catal. 2008; 350: 2881
- 4d ten Brink G.-J, Fernandes BC. M, van Vliet MC. A, Arends IW. C. E, Sheldon RA. J. Chem. Soc., Perkin Trans. 1 2001; 224
- 4e ten Brink G.-J, Vis J.-M, Arends IW. C. E, Sheldon RA. J. Org. Chem. 2001; 66: 2429
- 5a Yang Y, Fan X, Cao H, Chu S, Zhang X, Xu Q, Yu L. Catal. Sci. Technol. 2018; 8: 5017
- 5b Wang T, Jing X, Chen C, Yu L. J. Org. Chem. 2017; 82: 9342
- 5c Jing X, Yuan D, Yu L. Adv. Synth. Catal. 2017; 359: 1194
- 5d Jing X, Wang T, Ding Y, Yu L. Appl. Catal., A 2017; 541: 107
- 5e Wang F, Xu L, Sun C, Xu Q, Huang J, Yu L. Youji Huaxue 2017; 37: 2115
- 5f Wang Y, Yu L, Zhu B, Yu L. J. Mater. Chem. A 2016; 4: 10828
- 5g Yu L, Bai Z, Zhang X, Zhang X, Ding Y, Xu Q. Catal. Sci. Technol. 2016; 6: 1804
- 5h Yu L, Chen F, Ding Y. ChemCatChem 2016; 8: 1033
- 5i Yu L, Ye J, Zhang X, Ding Y, Xu Q. Catal. Sci. Technol. 2015; 5: 4830
- 5j Zhang X, Sun J, Ding Y, Yu L. Org. Lett. 2015; 17: 5840
- 5k Zhang X, Ye J, Yu L, Shi X, Zhang M, Xu Q, Lautens M. Adv. Synth. Catal. 2015; 357: 955
- 5l Yu L, Wu Y, Cao H, Zhang X, Shi X, Luan J, Chen T, Pan Y, Xu Q. Green Chem. 2014; 16: 287
- 5m Yu L, Li H, Zhang X, Ye J, Liu J, Xu Q, Lautens M. Org. Lett. 2014; 16: 1346
- 5n Yu L, Wang J, Chen T, Wang Y, Xu Q. Appl. Organomet. Chem. 2014; 28: 652
- 5o Yu L, Wang J, Chen T, Ding K, Pan Y. Youji Huaxue 2013; 33: 1096
- 6 Rayman MP. Lancet 2012; 379: 1256
- 7 Meotti FC, Borges VC, Zeni G, Rocha JB. T, Nogueira CW. Toxicol. Lett. 2003; 143: 9
- 8a Baker CO, Huang X.-W, Nelson W, Kaner RB. Chem. Soc. Rev. 2017; 46: 1510
- 8b Han J, Wang M, Hu Y, Zhou C, Guo R. Prog. Polym. Sci. 2017; 70: 52
- 8c Sen T, Mishra S, Shimpi NG. RSC Adv. 2016; 6: 42196
- 9a Oh W.-K, Kim S, Kwon O, Jang J. J. Nanosci. Nanotechnol. 2011; 11: 4254
- 9b Zhao H, Zhu B, Sekine J, Luo S, Yu H. ACS Appl. Mater. Interfaces 2012; 4: 680
- 10a Zhou C, Ren Y, Han J, Gong X, Wei Z, Xie J, Guo R. J. Am. Chem. Soc. 2018; 140: 9417
- 10b Liu Y, Tang D, Cao K, Yu L, Han J, Xu Q. J. Catal. 2018; 360: 250
- 10c Uozumi Y, Yamada YM. A, Yoshida H. Synfacts 2017; 13: 430
- 10d Yu L, Han Z, Ding Y. Org. Process Res. Dev. 2016; 20: 2124
- 10e Yu L, Huang Y, Wei Z, Ding Y, Su C, Xu Q. J. Org. Chem. 2015; 80: 8677
- 11a Zhang F, Zhang Y, Zhang G, Yang Z, Dionysiou DD, Zhu A. Appl. Catal., B 2018; 236: 53
- 11b Wu R.-H, Tsai M.-J, Ho K.-S, Wei T.-E, Hsieh T.-W, Han Y.-K, Kuo C.-W, Tseng P.-H, Wang Y.-Z. Polymer 2014; 55: 2035
- 11c Tumma M, Srivastava R. Catal. Commun. 2013; 37: 64
- 11d Palaniappan S, Rajender B. Adv. Synth. Catal. 2010; 352: 2507
- 11e Likhar PR, Roy M, Roy S, Subhas MS, Kantam ML, Sreedhar B. Adv. Synth. Catal. 2008; 350: 1968
- 11f Velusamy S, Ahamed M, Punniyamurthy T. Org. Lett. 2004; 6: 4821
- 12a Moon DK, Osakata K, Maruyama T, Yamamoto T. Makromol. Chem. 1992; 193: 1723
- 12b Liu C.-F, Moon D.-K, Maruyama T, Yamamoto T. Polym. J. (Tokyo, Jpn.) 1993; 25: 775
- 12c Sun Z, Geng Y, Li J, Jing X, Wang F. Synth. Met. 1997; 84: 99
- 12d Sun Z, Geng Y, Li J, Wang X, Jing X, Wang F. J. Appl. Polym. Sci. 1999; 72: 1077
- 12e Sivakumar M, Gedanken A. Synth. Met. 2005; 148: 301
- 13 Surwade SP, Agnihotra SR, Dua V, Manohar N, Jain S, Ammu S, Manohar SK. J. Am. Chem. Soc. 2009; 131: 12528
- 14 Polyaniline (2a); Typical ProcedurePhNH2 (8.8 mmol), H2O2 (4.4 mmol), and (4-TolSe)2 (0.1 mmol) were dissolved in 1 M aq HCl (100 mL), and the mixture was kept at 20 °C for 1 d. The precipitated polymer was isolated by filtration and washed with deionized H2O and EtOH. It was then dried at 65 °C under vacuum to give a dark-green solid; yield: 82%. FTIR (film): 3224, 3049, 2827, 2569, 1565, 1491, 1287, 1154, 826, 741, 690, 497 cm–1.
- 15a Wei Y, Hsueh KF, Jang G.-W. Polymer 1994; 35: 3572
- 15b Nicolas-Debarnot D, Poncin-Epaillard F. Anal. Chim. Acta 2003; 475: 1
- 16 Zhao D, Johansson M, Bäckvall J.-E. Eur. J. Org. Chem. 2007; 4431
For selected articles, please see:
For reviews, please see:
For selected articles, see:
For selected articles on organoselenium-catalyzed green reactions, see:
For our works on Se catalysis, see:
For reviews, see:
For previous works on oxidative polymerization of aniline with H2O2, see: