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Synthesis 2017; 49(07): 1623-1631
DOI: 10.1055/s-0036-1588921
DOI: 10.1055/s-0036-1588921
paper
Regioselective Radical Arylation of Aromatic Diamines with Arylhydrazines
Further Information
Publication History
Received: 15 October 2016
Accepted after revision: 14 November 2016
Publication Date:
07 December 2016 (online)
Abstract
The arylation of aromatic diamines with arylhydrazine hydrochlorides was achieved in reasonable yields. This new and simple reaction occurred at room temperature in air using an inexpensive base. This transformation seems to proceed via a homolytic aromatic substitution (HAS) mechanism. The synthesized aromatic diamines are used as raw materials for polyimides, including important aerospace materials, for example, Kapton®.
Key words
C–H arylation - aromatic diamine - homolytic aromatic substitution - arylhydrazine - 4,4′-diaminodiphenyl ether - Kapton®Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588921.
- Supporting Information
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References
- 1a Ni H.-J, Liu J.-G, Wang Z.-H, Yang S.-Y. J. Ind. Eng. Chem. 2015; 28: 16
- 1b Vanherck K, Koeckelberghs G, Vankelecom IF. J. Prog. Polym. Sci. 2013; 38: 874
- 1c Ghosh A, Sen SK, Banerjee S, Voit B. RSC Adv. 2012; 2: 5900
- 1d Wilson WC, Atkinson GM. NASA Technical Memorandum, Report Number: NASA/TM-2007-214870. 2007; ; http://ntrs.nasa.gov/search.jsp?R=20070018345
- 1e Sroog CE, Endrey AL, Abramo SV, Berr CE, Edwards WM, Olivier KL. J. Polym. Sci., Part A 1965; 3: 1373
- 2a Toney MF, Russell TP, Logan JA, Kikuchi H, Sands JM, Kumar SK. Nature 1995; 374: 709
- 2b Oh-e M, Hong S.-C, Shen YR. J. Phys. Chem. B 2000; 104: 7455
- 3a Yokota R, Miyauchi M, Ishida Y. Int. J. Soc. Mater. Eng. Resour. 2014; 20: 65
- 3b Yokota R, Yamamoto S, Yano S, Sawaguchi T, Hasegawa M, Yamaguchi H, Ozawa H, Sato R. High Perform. Polym. 2001; 13: 61
- 4a Hasegawa M, Sensui N, Shindo Y, Yokota R. Macromolecules 1999; 32: 387
- 4b Yokota R. J. Network Polym. Jpn. 2006; 27: 221
- 5a Lin CH, Chang SL, Peng LA, Peng SP, Chuang YH. Polymer 2010; 51: 3899
- 5b Zhao J, Peng L, Zhu Y.-L, Song Y.-J, Wang L.-J, Shen Y.-Z. Polymer 2016; 91: 118
- 5c Bu QQ, Zhang SJ, Li H, Li YF. Chin. Chem. Lett. 2012; 23: 121
- 5d Zhao J, Peng L, Zhu Y.-L, Zheng A.-M, Shen Y.-Z. Polym. Chem. 2016; 7: 1765
- 5e Mushtaq N, Chen G, Sidra LR, Fang X. RSC Adv. 2016; 6: 25302
- 6a Miyauchi M, Kazama K, Sawaguchi T, Yokota R. Polym. J. 2011; 43: 866
- 6b Miyauchi M, Ishida Y, Ogasawara T, Yokota R. Polym. J. 2012; 44: 959
- 6c Miyauchi M, Ishida Y, Ogasawara T, Yokota R. React. Funct. Polym. 2013; 73: 340
- 7 Chen J.-C, Wu J.-A, Chang H.-W, Lee C.-Y. Polym. Int. 2014; 63: 352
- 8a Heck RF. J. Am. Chem. Soc. 1968; 90: 5518
- 8b Heck RF. J. Am. Chem. Soc. 1968; 90: 5526
- 8c Heck RF. J. Am. Chem. Soc. 1968; 90: 5531
- 8d Heck RF. J. Am. Chem. Soc. 1968; 90: 5535
- 8e Heck RF. J. Am. Chem. Soc. 1968; 90: 5538
- 8f Heck RF. J. Am. Chem. Soc. 1968; 90: 5542
- 9a Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
- 9b Miyaura N, Suzuki A. J. Chem. Soc., Chem. Commun. 1979; 866
- 10a Negishi E.-I, King AO, Okukado N. J. Org. Chem. 1977; 42: 1821
- 10b King AO, Okukado N, Negishi E.-I. J. Chem. Soc., Chem. Commun. 1977; 683
- 11a Minisci F, Vismara E, Fontana F. Heterocycles 1989; 28: 489
- 11b Minisci F. Top. Curr. Chem. 1976; 62: 1
- 11c Harrowven DC, Sutton BJ. Prog. Heterocycl. Chem. 2004; 16: 27
- 11d Studer A, Bossart M In Radicals in Organic Synthesis . Vol. 2. Renaud P, Sibi MP. Wiley-VCH; Weinheim: 2001: 62
- 11e Fossey J, Lefort D, Sorba J In Free Radicals in Organic Chemistry . Wiley; Chichester: 1995: 167
- 11f Fehler SK, Heinrich MR. Synlett 2015; 26: 580
- 11g Sun C.-L, Shi Z.-J. Chem. Rev. 2014; 114: 9219 ; and references cited therein
- 12 Gomberg M, Bachmann ME. J. Am. Chem. Soc. 1924; 46: 2339
- 13a Dewanji A, Murarka S, Curran DP, Studer A. Org. Lett. 2013; 15: 6102
- 13b Patil P, Nimonkar A, Akamanchi KG. J. Org. Chem. 2014; 79: 2331
- 13c Xiao T, Li L, Lin G, Wang Q, Zhang P, Mao Z, Zhou L. Green Chem. 2014; 16: 2418
- 13d Jiang T, Chen S.-Y, Zhang G.-Y, Zeng R.-S, Zou J.-P. Org. Biomol. Chem. 2014; 12: 6922
- 13e Yu J, Wang S, Wen J, Wang J, Li J.-H. Synlett 2015; 26: 1121
- 13f Li Y, Liu W, Kuang C. Chem. Commun. 2014; 50: 7124
- 13g Ravi M, Chauhan P, Kant R, Shukla SK, Yadav PP. J. Org. Chem. 2015; 80: 5369
- 14a Wetzel A, Ehrhardt V, Heinrich MR. Angew. Chem. Int. Ed. 2008; 47: 9130
- 14b Wetzel A, Pratsch G, Kolb R, Heinrich MR. Chem. Eur. J. 2010; 16: 2547
- 14c Jasch H, Scheumann J, Heinrich MR. J. Org. Chem. 2012; 77: 10699
- 14d Hammer SG, Heinrich MR. Tetrahedron 2014; 70: 8114
- 14e Hofmann J, Jasch H, Heinrich MR. J. Org. Chem. 2014; 79: 2314
- 14f Jiang T, Chen S.-Y, Zhuang H, Zeng R.-S, Zou J.-P. Tetrahedron Lett. 2014; 55: 4549
- 14g Zhang X. Int. J. Quant. Chem. 2015; 115: 1658
- 14h Hofmann D, Hofmann J, Hofmann L.-E, Hofmann L, Heinrich MR. Org. Process Res. Dev. 2015; 19: 2075
- 15 Taniguchi T, Imoto M, Takeda M, Matsumoto F, Nakai T, Mihara M, Mizuno T, Nomoto A, Ogawa A. Tetrahedron 2016; 72: 4132
For reviews on HAS reactions, please see: