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RESEARCH ARTICLE
Contents Vol 72(7)

Cellulose-Supported Ionic Liquid Phase Catalyst-Mediated Mannich Reaction

Sharanabasappa Khanapure A , Megha Jagadale A , Dolly Kale A , Shivanand Gajare A and Gajanan Rashinkar A B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, Shivaji University, Kolhapur, 416004, India.

B Corresponding author. Email: gsr_chem@unishivaji.ac.in

Australian Journal of Chemistry 72(7) 513-523 https://doi.org/10.1071/CH18576
Submitted: 22 November 2018  Accepted: 18 March 2019   Published: 30 April 2019

Abstract

Cellulose-supported ionic liquid phase (SILP) catalyst containing a camphor sulfonate anion with a pendant ferrocenyl group was prepared and characterised with different analytical techniques such as Fourier-transform infrared, Fourier-transform Raman, and cross polarization–magic angle spinning (CP-MAS) 13C NMR spectroscopy, X-ray diffraction, scanning electron microscopy, and thermogravimetric analysis. The SILP catalyst displayed excellent catalytic activity in the synthesis of β-amino carbonyl compounds by Mannich reaction. Recycling studies revealed that SILP catalyst could be reused six times without significant decrease in catalytic activity.


References

[1]  T. Welton, Chem. Rev. 1999, 99, 2071.
         | Crossref | GoogleScholarGoogle Scholar | 11849019PubMed |

[2]  C. P. Mehnert, R. A. Cook, N. C. Dispenziere, M. Afeworki, J. Am. Chem. Soc. 2002, 124, 12932.
         | Crossref | GoogleScholarGoogle Scholar | 12405804PubMed |

[3]  B. Xin, J. Hao, Chem. Soc. Rev. 2014, 43, 7171.
         | Crossref | GoogleScholarGoogle Scholar | 25000475PubMed |

[4]  M. Mirzaei, A. Badiei, B. Mokhtarani, A. Sharifi, J. Mol. Liq. 2017, 232, 462.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  N. Gathergood, P. J. Scammells, Aust. J. Chem. 2002, 55, 557.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  C. Van Doorslaer, J. Wahlen, P. Mertens, K. Binnemans, D. De Vos, Dalton Trans. 2010, 39, 8377.
         | Crossref | GoogleScholarGoogle Scholar | 20419187PubMed |

[7]  A. Riisager, R. Fehrmann, M. Haumann, P. Wasserscheid, Top. Catal. 2006, 40, 91.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  P. Sharma, M. Gupta, M. Gupta, R. Gupta, Aust. J. Chem. 2016, 69, 230.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  A. Riisager, R. Fehrmann, M. Haumann, P. Wasserscheid, Eur. J. Inorg. Chem. 2006, 695.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  M. Zhang, Q. Sun, Z. Yan, J. Jing, W. Wei, D. Jiang, J. Xie, M. Chen, Aust. J. Chem. 2013, 66, 564.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  H. Li, P. S. Bhadury, B. Song, S. Yang, RSC Adv. 2012, 2, 12525.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  M. I. Burguete, H. Erythropel, E. Garcia-Verdugo, S. V. Luis, V. Sans, Green Chem. 2008, 10, 401.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  M. A. Gelesky, S. S. X. Chiaro, F. A. Pavan, J. H. Z. dos Santos, J. Dupont, Dalton Trans. 2007, 5549.
         | Crossref | GoogleScholarGoogle Scholar | 18043816PubMed |

[14]  T. Takeshita, A. Kitagawa, F. Yokosu, R. Matsumoto, T. Nokami, T. Itoh, Aust. J. Chem. 2019, 72, 61.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  G. Rashinkar, R. Salunkhe, J. Mol. Catal. Chem. 2010, 316, 146.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  R.-Q. Yang, N. Zhang, X.-G. Meng, X.-H. Liao, L. Li, H.-J. Song, Aust. J. Chem. 2018, 71, 559.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  V. Sans, N. Karbass, M. I. Burguete, V. Compan, E. Garcia-Verdugo, S. V. Luis, M. Pawlak, Chem. – Eur. J. 2011, 17, 1894.
         | Crossref | GoogleScholarGoogle Scholar | 21274940PubMed |

[18]  D. Kale, G. Rashinkar, A. Kumbhar, R. Salunkhe, React. Funct. Polym. 2017, 116, 9.
         | Crossref | GoogleScholarGoogle Scholar |

[19]  M. Jagadale, S. Khanapure, R. Salunkhe, M. Rajmane, G. Rashinkar, Appl. Organomet. Chem. 2016, 30, 125.
         | Crossref | GoogleScholarGoogle Scholar |

[20]  A. Rahmatpour, React. Funct. Polym. 2011, 71, 80.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  L. Rodríguez-Pérez, E. Teuma, A. Falqui, M. Gómez, P. Serp, Chem. Commun. 2008, 4201.
         | Crossref | GoogleScholarGoogle Scholar |

[22]  J.-P. Mikkola, P. Virtanen, H. Karhu, T. Salmi, D. Y. Murzin, Green Chem. 2006, 8, 197.
         | Crossref | GoogleScholarGoogle Scholar |

[23]  N. Clousier, R. Moucel, P. Naik, P.-J. Madec, A. C. Gaumont, I. Dez, C. R. Chim. 2011, 14, 680.
         | Crossref | GoogleScholarGoogle Scholar |

[24]  Y. Qiao, H. Li, L. Hua, L. Orzechowski, K. Yan, B. Feng, Z. Pan, N. Theyssen, W. Leitner, Z. Hou, ChemPlusChem 2012, 77, 1128.
         | Crossref | GoogleScholarGoogle Scholar |

[25]  L. Berglund, A. Bismarck, A. Dufresne, A. Isogai, React. Funct. Polym. 2014, 85, 77.
         | Crossref | GoogleScholarGoogle Scholar |

[26]  M. Sharifi, S.-M. Robatjazi, M. Sadri, J. M. Mosaabadi, React. Funct. Polym. 2018, 124, 162.
         | Crossref | GoogleScholarGoogle Scholar |

[27]  D. Fenn, M. Pohl, T. Heinze, React. Funct. Polym. 2009, 69, 347.
         | Crossref | GoogleScholarGoogle Scholar |

[28]  X. Chen, J. Chen, T. You, K. Wang, F. Xu, Carbohydr. Polym. 2015, 125, 85.
         | Crossref | GoogleScholarGoogle Scholar | 25857963PubMed |

[29]  A. Mohammadinezhad, M. A. Nasseri, M. Salimi, RSC Adv. 2014, 4, 39870.
         | Crossref | GoogleScholarGoogle Scholar |

[30]  A. Shaabani, Z. Hezarkhani, S. Shaabani, RSC Adv. 2014, 4, 64419.
         | Crossref | GoogleScholarGoogle Scholar |

[31]  D. Baruah, U. P. Saikia, P. Pahari, D. K. Dutta, D. Konwar, RSC Adv. 2014, 4, 59338.
         | Crossref | GoogleScholarGoogle Scholar |

[32]  F. Quignard, A. Choplin, Chem. Commun. 2001, 21.
         | Crossref | GoogleScholarGoogle Scholar |

[33]  Y. Habibi, L. A. Lucia, O. J. Rojas, Chem. Rev. 2010, 110, 3479.
         | Crossref | GoogleScholarGoogle Scholar | 20201500PubMed |

[34]  C. Tsioptsias, A. Stefopoulos, I. Kokkinomalis, L. Papadopoulou, C. Panayiotou, Green Chem. 2008, 10, 965.
         | Crossref | GoogleScholarGoogle Scholar |

[35]  R. Müller, H. Goesmann, H. Waldmann, Angew. Chem. Int. Ed. 1999, 38, 184.
         | Crossref | GoogleScholarGoogle Scholar |

[36]  K. Mogilaiah, G. Kankaiah, Indian J. Heterocycl. Chem. 2002, 11, 283.

[37]  F. A. Davis, M. B. Nolt, Y. Wu, K. R. Prasad, D. Li, B. Yang, K. Bowen, S. H. Lee, J. H. Eardley, J. Org. Chem. 2005, 70, 2184.
         | Crossref | GoogleScholarGoogle Scholar | 15760203PubMed |

[38]  A. G. Khiratkar, K. R. Balinge, K. J. Bhansali, P. R. Bhagat, Res. Chem. Intermed. 2018, 44, 787.
         | Crossref | GoogleScholarGoogle Scholar |

[39]  A. Davoodnia, A. Tavakoli-Nishaburi, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 2011, 32, 635.
         | Crossref | GoogleScholarGoogle Scholar |

[40]  H. Li, H.-Y. Zeng, H.-W. Shao, Tetrahedron Lett. 2009, 50, 6858.
         | Crossref | GoogleScholarGoogle Scholar |

[41]  S. Iimura, D. Nobutou, K. Manabe, S. Kobayashi, Chem. Commun. 2003, 1644.
         | Crossref | GoogleScholarGoogle Scholar |

[42]  S. Ramalingam, P. Kumar, Catal. Commun. 2008, 9, 2445.
         | Crossref | GoogleScholarGoogle Scholar |

[43]  N. Azizi, L. Torkiyan, M. R. Saidi, Org. Lett. 2006, 8, 2079.
         | Crossref | GoogleScholarGoogle Scholar | 16671786PubMed |

[44]  R. Kurane, J. Jadhav, S. Khanapure, R. Salunkhe, G. Rashinkar, Green Chem. 2013, 15, 1849.
         | Crossref | GoogleScholarGoogle Scholar |

[45]  A. Naikwade, M. Jagadale, D. Kale, S. Gajare, G. Rashinkar, Catal. Lett. 2018, 148, 3178.
         | Crossref | GoogleScholarGoogle Scholar |

[46]  U. P. R. Filho, Y. Gushikem, F. Y. Fujiwara, S. C. de Castro, I. C. L. Torriani, L. P. Cavalcanti, Langmuir 1994, 10, 4357.
         | Crossref | GoogleScholarGoogle Scholar |

[47]  A. Bhattacharya, B. N. Misra, Prog. Polym. Sci. 2004, 29, 767.
         | Crossref | GoogleScholarGoogle Scholar |

[48]  Y. Wu, Z. Fu, D. Yin, Q. Xu, F. Liu, C. Lu, L. Mao, Green Chem. 2010, 12, 696.
         | Crossref | GoogleScholarGoogle Scholar |

[49]  O. W. Guirguis, M. T. H. Moselhey, Nat. Sci. 2012, 4, 57.

[50]  M. Sevilla, A. B. Fuertes, Carbon 2009, 47, 2281.
         | Crossref | GoogleScholarGoogle Scholar |

[51]  K. Nobuoka, S. Kitaoka, K. Kunimitsu, M. Iio, T. Harran, A. Wakisaka, Y. Ishikawa, J. Org. Chem. 2005, 70, 10106.
         | Crossref | GoogleScholarGoogle Scholar | 16292848PubMed |

[52]  Metallocenes (Eds A. Togni, R. L. Halterman) 1998 (Wiley-VCH, Verlag GmbH: Weinheim).

[53]  Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Material Science (Eds A. Togni, T. Hayashi) 1995 (Wiley-VCH, Verlag GmbH: Weinheim).

[54]  R. C. Atkinson, V. C. Gibson, N. J. Long, Chem. Soc. Rev. 2004, 33, 313.
         | Crossref | GoogleScholarGoogle Scholar | 15272371PubMed |

[55]  P. Barbaro, C. Bianchini, G. Gianbastini, S. L. Parisel, Coord. Chem. Rev. 2004, 248, 2131.
         | Crossref | GoogleScholarGoogle Scholar |

[56]  U. Siemeling, T.-C. Auch, Chem. Soc. Rev. 2005, 34, 584.
         | Crossref | GoogleScholarGoogle Scholar | 15965540PubMed |

[57]  T. J. Colacot, Platin. Met. Rev. 2001, 45, 22.

[58]  Y. Gao, B. Twamley, J. M. Shreeve, Inorg. Chem. 2004, 43, 3406.
         | Crossref | GoogleScholarGoogle Scholar | 15154802PubMed |

[59]  V. K. Ahluwalia, R. Aggarwal, Comprehensive Practical Organic Chemistry: Preparations and Quantitative Analysis 2005 (Universities Press (India) Pvt Limited: Hyderabad, Telangana).

[60]  A. Kumbhar, S. Jadhav, R. Shejwal, G. Rashinkar, R. Salunkhe, RSC Adv. 2016, 6, 19612.
         | Crossref | GoogleScholarGoogle Scholar |

[61]  K. Kundu, S. K. Nayak, RSC Adv. 2012, 2, 480.
         | Crossref | GoogleScholarGoogle Scholar |