Protic ionic liquids as catalysts for a three-component coupling/hydroarylation/dehydrogenation tandem reaction

Maren Muntzeck 1  and René Wilhelm 2
  • 1 Department of Chemistry, University of Paderborn, Warburger Straße 100, 33098 Paderborn, Germany
  • 2 Department of Chemistry, University of Paderborn, Warburger Straße 100, 33098 Paderborn, Germany
Maren Muntzeck
  • Department of Chemistry, University of Paderborn, Warburger Straße 100, 33098 Paderborn, Germany
  • Search for other articles:
  • degruyter.comGoogle Scholar
and René Wilhelm
  • Corresponding author
  • Department of Chemistry, University of Paderborn, Warburger Straße 100, 33098 Paderborn, Germany
  • Email
  • Search for other articles:
  • degruyter.comGoogle Scholar

Abstract

Protic ionic liquids with nitrate anions were used as solvents and catalysts for a three-component oxidative dehydrogenation tandem reaction via the coupling and hydroarylation of benzaldehyde, aniline, and phenylacetylene to a quinoline derivative. The reaction was supported by air and microwave irradiation. The presence of nitrate as counter anion in the protic ionic liquids was essential for the reaction.

  • [1]

    P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis, 2nd edition, Vol. 1–2, Wiley-VCH, Weinheim, 2008.

  • [2]

    R. D. Rogers, K. R. Seddon, Ionic Liquids as Green Solvents: Progress and Prospects, American Chemical Society, Washington, DC, 2003, p. 2.

  • [3]

    T. Welton, Chem. Rev. 1999, 99, 2071.

  • [4]

    D. Zhao, M. Wu, Y. Kou, E. Min, Catal. Today 2002, 74, 157.

    • Crossref
    • Export Citation
  • [5]

    C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A. C. Gaumont, J. C. Plaquevent, Tetrahedron: Asymmetry 2003, 14, 3081.

    • Crossref
    • Export Citation
  • [6]

    N. Jain, A. Kumar, S. Chauhan, S. M. S. Chauhan, Tetrahedron 2005, 61, 1015.

    • Crossref
    • Export Citation
  • [7]

    V. I. Parvulescu, C. Hardacre, Chem. Rev. 2007, 107, 2615.

  • [8]

    J. Durand, E. Teuma, M. Goez, C. R. Chim. 2007, 10, 152.

  • [9]

    J. Muzart, Adv. Synth. Catal. 2006, 348, 275.

  • [10]

    O. Sereda, S. Tabassum, R. Wilhelm, Top. Curr. Chem. 2010, 291, 349.

  • [11]

    P. Walden, Bull. Acad. Imper. Sci. 1914, 1800.

  • [12]

    T. L. Greaves, C. J. Drummond, Chem. Rev. 2008, 108, 206.

  • [13]

    T. L. Greaves, C. J. Drummond, Chem. Rev. 2015, 115, 11379.

  • [14]

    A. R. Hajipour, F. Rafiee, Org. Prep. Proc. Int. 2010, 42, 285.

    • Crossref
    • Export Citation
  • [15]

    H.-P. Zhu, F. Yang, J. Tang, M.-Y. He, Green Chem. 2003, 5, 38.

  • [16]

    H. Zhang, F. Xu, X. Zhou, G. Zhang, C. Wang, Green Chem. 2007, 9, 1208.

    • Crossref
    • Export Citation
  • [17]

    P. A. Ganeshpure, G. George, J. Das, J. Mol. Catal. A: Chem. 2008, 279, 182.

    • Crossref
    • Export Citation
  • [18]

    I. Cota, R. Gonzalez-Olmos, M. Iglesias, F. Medina, J. Phys. Chem. B 2007, 111, 12468.

    • Crossref
    • PubMed
    • Export Citation
  • [19]

    Y. Q. Li, X. M. Xu, M. Y. Zhou, Chin. Chem. Lett. 2003, 14, 448.

  • [20]

    R. V. Hangarge, D. V. Jarikote, M. S. Shingare, Green Chem. 2002, 4, 266.

    • Crossref
    • Export Citation
  • [21]

    C. G. Adam, G. G. Fortunato, P. M. Mancini, J. Phys. Org. Chem. 2009, 22, 460.

    • Crossref
    • Export Citation
  • [22]

    S. A. R. Mulla, T. A. Salama, M. Y. Pathan, S. M. Inamdar, S. S. Chavan, Tetrahedron Lett. 2013, 54, 672.

    • Crossref
    • Export Citation
  • [23]

    K. M. Deshmukh, Z. S. Qureshi, Y. P. Patil, B. M. Bhanage, Synth. Commun. 2012, 42, 93.

    • Crossref
    • Export Citation
  • [24]

    K. K. Laali, V. J. Gettwert, J. Org. Chem. 2001, 66, 35.

  • [25]

    N. L. Lancaster, V. Llopis-Mestre, Chem. Commun. 2003, 2812.

  • [26]

    E. Dal, N. L. Lancaster, Org. Biomol. Chem. 2005, 3, 682.

  • [27]

    K. Smith, S. Liu, G. A. El-Hiti, Ind. Eng. Chem. Res. 2005, 44, 8611.

    • Crossref
    • Export Citation
  • [28]

    Q. Kun, Y. Chiaki, Chem. Lett. 2004, 33, 808.

  • [29]

    M. J. Earle, S. P. Katdare, K. R. Seddon, Org. Lett. 2004, 6, 707.

  • [30]

    A. R. Hajipour, F. Rafiee, A. E. Ruoho, Synlett 2007, 1118.

  • [31]

    L. D. S. Yadav, C. Awashti, A. Rai, Tetrahedron Lett. 2008, 49, 6360.

    • Crossref
    • Export Citation
  • [32]

    S. Shi, A. Kong, X. Zhao, Y. Shan, Synth. Commun. 2011, 41, 3066.

    • Crossref
    • Export Citation
  • [33]

    C. Chiappe, E. Leandri, M. Tebano, Green Chem. 2006, 8, 742.

  • [34]

    A. Mirjafari, N. Mobarrez, R. A. O’Brien, J. H. Davis Jr, J. Noei, C. R. Chim. 2011, 14, 1065.

    • Crossref
    • Export Citation
  • [35]

    V. Jurčík, R. Wilhelm, Green Chem. 2005, 7, 844.

  • [36]

    V. Jurčík, R. Wilhelm, Tetrahedron: Asymmetry 2006, 17, 801.

    • Crossref
    • Export Citation
  • [37]

    V. Jurčík, M. Gilani, R. Wilhelm, Eur. J. Org. Chem. 2006, 5103.

  • [38]

    A. Winkel, R. Wilhelm, Tetrahedron: Asymmetry 2009, 20, 2344.

    • Crossref
    • Export Citation
  • [39]

    A. Winkel, R. Wilhelm, Eur. J. Org. Chem. 2010, 5817.

  • [40]

    A. Blanrue, R. Wilhelm, Synthesis 2009, 583.

  • [41]

    V. Jurčík, R. Wilhelm, Org. Biomol. Chem. 2005, 3, 239.

  • [42]

    O. Sereda, N. Clemens, T. Heckel, R. Wilhelm, Beilstein J. Org. Chem. 2012, 8, 1798.

    • Crossref
    • PubMed
    • Export Citation
  • [43]

    T. Heckel, D. D. Konieczna, R. Wilhelm, Catalysts 2013, 3, 914.

  • [44]

    T. Heckel, A. Winkel, R. Wilhelm, Tetrahedron: Asymmetry 2013, 24, 1127.

    • Crossref
    • Export Citation
  • [45]

    M. Muntzeck, R. Wilhelm, Int. J. Mol. Sci. 2016, 17, 860.

  • [46]

    Y. L. Chen, K. C. Fang, J. Y. Sheu, S. L. Hsu, C. C. Tzeng, J. Med. Chem. 2001, 44, 2374.

    • Crossref
    • PubMed
    • Export Citation
  • [47]

    J. P. Michael, Nat. Prod. Rep. 1997, 14, 605.

  • [48]

    I. Solomonov, M. Osipova, Y. Feldman, C. Baehtz, K. Kjaer, I. K. Robinson, G. T. Webster, D. McNaughton, B. R. Wood, I. Weissbuch, L. Leiserowitz, J. Am. Chem. Soc. 2007, 129, 2615.

    • Crossref
    • PubMed
    • Export Citation
  • [49]

    P. G. Dormer, K. K. Eng, R. N. Farr, G. R. Humphrey, J. C. McWilliams, P. J. Reider, J. W. Sager, R. P. Volante, J. Org. Chem. 2003, 68, 467.

    • Crossref
    • PubMed
    • Export Citation
  • [50]

    Y. Hsiao, N. R. Rivera, N. Yasuda, D. L. Hughes, P. J. Reider, Org. Lett. 2001, 3, 1101.

    • Crossref
    • PubMed
    • Export Citation
  • [51]

    Y. Z. Hu, D. Zhang, R. P. Thumme, Org. Lett. 2003, 5, 2251.

  • [52]

    B. R. McNaughton, B. L. Miller, Org. Lett. 2003, 5, 4257.

  • [53]

    H. Cho, F. Torok, B. Torok, Green Chem. 2014, 16, 3623.

  • [54]

    Y. Kuninobu, Y. Inoue, K. Takai, Chem. Lett. 2007, 36, 1422.

  • [55]

    J. Tang, L. M. Wang, D. Mao, W. B. Wang, L. Zhang, S. Y. Wu, Y. S. Xie, Tetrahedron 2011, 67, 8465.

    • Crossref
    • Export Citation
  • [56]

    F. P. Xiao, Y. L. Chen, Y. Liu, J. B. Wang, Tetrahedron 2008, 64, 2755.

    • Crossref
    • Export Citation
  • [57]

    X. Zhang, B. Q. Liu, X. Shu, Y. Gao, H. P. Lv, J. Zhu, J. Org. Chem. 2012, 77, 501.

  • [58]

    K. Cao, F. M. Zhang, Y. Q. Tu, X. T. Zhuo, C. A. Fan, Chem. Eur. J. 2009, 15, 6332.

    • Crossref
    • Export Citation
  • [59]

    S. S. Patil, S. V. Patil, V. D. Bobade, Synlett 2011, 2379.

  • [60]

    C. S. Yao, B. B. Qin, H. H. Zhang, J. Lu, D. L. Wang, S. J. Tu, RSC Adv. 2012, 2, 3759.

    • Crossref
    • Export Citation
  • [61]

    I. Bauer, H. J. Knölker, Chem. Rev. 2015, 115, 3170.

  • [62]

    A. Kumar, V. K. Rao, Synlett 2011, 2157.

  • [63]

    S. Thomaier, W. Kunz, J. Mol. Liq. 2007, 130, 104.

  • [64]

    T. L. Greaves, A. Weerawardena, I. Krodkiewska, C. J. Drummond, J. Phys. Chem. B 2008, 112, 896.

    • Crossref
    • PubMed
    • Export Citation
  • [65]

    J.-H. Lin, C.-P. Zhang, Z.-Q. Zhu, Q.-Y. Chen, J.-C. Xiao, J. Fluor. Chem. 2009, 130, 394.

    • Crossref
    • Export Citation
  • [66]

    H. Ono, S. Ishimaru, R. Ikeda, H. Ishida, Chem. Phys. Lett. 1997, 275, 485.

    • Crossref
    • Export Citation
  • [67]

    V. N. Emel’yanenko, S. P. Verevkin, A. Heintz, K. Voss, A. Schulz, J. Phys. Chem. B 2009, 113, 9871.

    • Crossref
    • PubMed
    • Export Citation
  • [68]

    P. Attri, P. M. Reddy, P. Venkatesu, A. Kumar, T. Hofman, J. Phys. Chem. B 2010, 114, 6126.

    • Crossref
    • PubMed
    • Export Citation
  • [69]

    G. L. Burrell, I. M. Burgar, F. Separovic, N. F. Dunlop, Phys. Chem. Chem. Phys. 2010, 12, 1571.

    • Crossref
    • PubMed
    • Export Citation
  • [70]

    E. Nagy, E. St. Germain, P. Cosme, P. Maity, A. C. Terentis, S. D. Lepore, Chem. Commun. 2016, 52, 2311.

    • Crossref
    • Export Citation
Purchase article
Get instant unlimited access to the article.
$42.00
Log in
Already have access? Please log in.


or
Log in with your institution

Journal + Issues

Zeitschrift für Naturforschung B is an international scientific journal which publishes original papers, microreviews, and letters from all areas of inorganic chemistry, solid state chemistry, coordination chemistry, molecular chemistry, and organic chemistry.

Search