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CC BY 4.0 · SynOpen 2023; 07(01): 121-129
DOI: 10.1055/a-2025-2759
paper

CN-Doped Cobalt Oxide Composite: An Economic and Reusable Catalyst with Multitasking Catalytic Capability for Alkyne and Nitrile Hydrations and Nitro Reductions

Avinash K. Srivastava
,
Himanshu Khandaka
,
Raj Kumar Joshi  ∗
Raj K. Joshi thanks the CSIR (Grant no. 01(2996)/19/EMR-II) for financial assistance.
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Abstract

A heterogeneous CoOCN composite was synthesized via a one-pot reaction of [Co(NO3)2] and urea at 500 °C in a muffle furnace. The composite was fully characterized by FTIR, Raman, powder XRD, and XPS techniques. The catalyst was found to be efficient for the hydrations of aryl alkynes and nitriles under aerobic conditions. In addition, the catalyst exhibits high catalytic performance for the reduction of nitroarenes under inert gas-free conditions. This multitasking CoOCN composite was found to be highly suitable for all derivatives of nitrobenzene, alkynes, and nitriles because good to excellent yields were obtained. The catalyst was recovered quantitatively from the reaction mixture by simple filtration and consequently reused for seven consecutive cycles in all reactions without significant loss of catalytic activity. Hence, the synthesized CN-doped CoOCN composite worked as a multitasking catalyst for various value-added organic transformations, and it is highly economical and reusable for up to seven catalytic cycles without any activation, with even the last cycle producing reasonable yields of up to 48–50%.

Key words

heterogeneous catalysts - cobalt oxide - alkyne hydration - nitrile hydration - nitro reduction - catalysis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2025-2759.
  • Supporting Information


Publication History

Received: 20 December 2022

Accepted after revision: 02 February 2023

Accepted Manuscript online:
02 February 2023

Article published online:
27 March 2023

© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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  • References

  • 1 Twilton J, Le CC, Zhang P, Shaw MH, Evans RW, Macmillan DW. C. Nat. Rev. Chem. 2017; 1: 0052
    CrossrefPubMed
  • 2 Justin-Besançon L, Castex MR. Prensa Med. Argent. 1969; 55: 1771
    PubMed
  • 3 Westerhaus FA, Jagadeesh RV, Wienhöfer G, Pohl MM, Radnik J, Surkus AE, Rabeah J, Junge K, Junge H, Nielsen M, Brückner A, Beller M. Nat. Chem. 2013; 5: 537
    CrossrefPubMed
  • 4 National Research Council, Catalysis Looks to the Future (Panel on New Directions in Catalytic Science and Technology) . The National Academies Press; Washington DC: 1992. DOI 10.17226/1903
    Google Scholar
  • 5 Handbook of Heterogeneous Catalysis, Vol. 1, 2nd ed. Ertl G, Knözinger H, Schüth F, Weitkamp J. Wiley-VCH; Weinheim: 2008
    Google Scholar
  • 6 Jagadeesh RV, Surkus AE, Junge H, Pohl MM, Radnik J, Rabeah J, Huan H, Schünemann V, Brückner A, Beller M. Science 2013; 342: 1073
    CrossrefPubMed
  • 7 Védrine JC. Catalysts 2017; 7: 341
    Crossref
  • 8 Hintermann L, Labonne A. Synthesis 2007; 1121
    Article in Thieme Connect
  • 9 Veer SD, Pathare SP, Akamanchi KG. ARKIVOC 2016; 4: 59
    Crossref
  • 10 Hennion GF, Vogt RR, Nieuwland JA. J. Org. Chem. 1936; 1: 159
    Crossref
  • 11 Mizushima E, Sato K, Hayashi T, Tanaka M. Angew. Chem. 2002; 114: 4745
    Crossref
    • 12a Ali M, Srivastava AK, Siangwata S, Smith GS, Joshi RK. Catal. Commun. 2018; 115: 78
      Crossref
    • 12b Srivastava AK, Ali M, Siangwata S, Satrawala N, Smith GS, Joshi RK. Asian J. Org. Chem. 2020; 9, 377
    • 12c Sharma C, Srivastava AK, Soni A, Kumari S, Joshi RK. RSC Adv. 2020; 10: 32516
      CrossrefPubMed
    • 13a Ali M, Srivastava AK, Joshi RK. Tetrahedron Lett. 2018; 59: 2075
      Crossref
    • 13b Suthar M, Srivastava AK, Sharma C, Joshi RK, Roy PK. Ceram. Int. 2022; 48: 37370
      Crossref
  • 14 Vasudevan A, Verzal MK. Synlett 2004; 631
    Article in Thieme ConnectPubMed
  • 15 Tachinami T, Nishimura T, Ushimaru R, Noyori R, Naka H. J. Am. Chem. Soc. 2013; 135: 50
    CrossrefPubMed
  • 16 Wang S, Miao C, Wang W, Lei Z, Sun W. Chin. J. Catal. 2014; 35: 1695
    CrossrefPubMed
  • 17 Lin Z, Zhang Z, Chen Y, Lin W. Angew. Chem. Int. Ed. 2016; 55: 13739
    CrossrefPubMed
  • 18 Hou S, Yang H, Cheng B, Zhai H, Li Y. Chem. Commun. 2017; 53: 6926
    CrossrefPubMed
  • 19 de Noronha RG, Romão CC, Fernandes AC. J. Org. Chem. 2009; 74: 6960
    CrossrefPubMed
  • 20 Berthold H, Schotten T, Hönig H. Synthesis 2002; 1607
    CrossrefPubMed
  • 21 Rahaim RJ, Maleczka RE. Org. Lett. 2005; 7: 5087
    CrossrefPubMed
  • 22 Mohapatra SK, Sonavane SU, Jayaram RV, Selvam P. Org. Lett. 2002; 4: 4297
    CrossrefPubMed
  • 23 Sharma U, Kumar P, Kumar N, Kumar V, Singh B. Adv. Synth. Catal. 2010; 352: 1834
    Crossref
  • 24 Agrawal A, Tratnyek PG. Environ. Sci. Technol. 1995; 30: 153
    CrossrefPubMed
  • 25 Khan FA, Sudheer C. Tetrahedron Lett. 2009; 50: 3394
    CrossrefPubMed
  • 26 Bae JW, Cho YJ, Lee SH, Yoon CO. M, Yoon CM. Chem. Commun. 2000; 1857
    Crossref
  • 27 Lin X, Wu M, Wu D, Kuga S, Endoe T, Huang Y. Green Chem. 2011; 13: 283
    CrossrefPubMed
  • 28 Junge K, Wendt B, Shaikh N, Beller M. Chem Commun. 2010; 46: 1769
    CrossrefPubMed
  • 29 Jagadeesh RV, Wienhöfer W, Westerhaus FA, Surkus AE, Pohl MM, Junge H, Junge K, Beller M. Chem. Commun. 2011; 47: 10972
    CrossrefPubMed
  • 30 Kim S, Kim E, Kim BM. Chem. Asian J. 2011; 6: 1921
    CrossrefPubMed
  • 31 Griffitts F, Brown O. J. Phys. Chem. 1937; 41: 477
    CrossrefPubMed
  • 32 Sun X, Olivos-Suarez AI, Osadchii D, Romero MJ. V, Kapteijn K, Gascon J. J. Catal. 2018; 357: 20
    CrossrefPubMed
  • 33 Unglaube F, Schlapp J, Quade A, Schafer J, Mejia E. Catal. Sci. Technnol. 2022; 12: 3123
    CrossrefPubMed
  • 34 Tao D.-J, Liu F, Wang L, Jiang L. Appl. Catal. A: General 2018; 564: 56
    CrossrefPubMed
  • 35 Gatto M, Baratta W, Belanzoni P, Belpassi L, Zotto A, Tarantelli F, Zuccaccia M. Green Chem. 2018; 20: 2125
    CrossrefPubMed
  • 36 Cloutier M, Roudias M, Paquin J.-F. J. Org. Lett. 2019; 21: 3866
    CrossrefPubMed
  • 37 He T, Chen D, Jiao X, Xu Y, Gu Y. Langmuir 2004; 20: 8404
    CrossrefPubMed
  • 38 Yu J, Wang K, Xiao W, Cheng B. Phys. Chem. Chem. Phys. 2014; 16: 11492
    CrossrefPubMed
  • 39 Zou H, Yan X, Ren J, Wu X, Dai Y, Sha D, Pan J, Liu J. J. Materiomics 2015; 1, 340
    CrossrefPubMed
  • 40 Farhadi S, Javanmard M, Nadri G. Acta Chim. Slov. 2016; 63: 335
    CrossrefPubMed
  • 41 Huang W, Ding S, Chen Y, Hao W, Lai X, Peng J, Tu J, Cao Y, Li X. Sci. Rep. 2017; 7: 5220
    CrossrefPubMed
  • 42 Rao AM, Eklund PC, Bandow S, Thess A, Smalley RE. Nature 1977; 388: 257
    Crossref
  • 43 Lai J, Liu Z, Chen X, Zhang H, Liu H. Tetrahedron Lett. 2020; 61: 152426
    Crossref
  • 44 Xie Y, Wang J, Wang Y, Han S, Yu H. ChemCatChem 2021; 13: 4985
    CrossrefPubMed
  • 45 Gangarajula Y, Gopal B. Chem. Lett. 2012; 41: 101
    CrossrefPubMed
  • 46 Wu X, Bezier D, Darcel C. Adv. Synth. Catal. 2009; 351: 367
    Crossref
  • 47 Li F, Wang N, Lu L, Zhu G. J. Org. Chem. 2015; 80: 3538
    CrossrefPubMed
  • 48 Kumar S, Das P. New J. Chem. 2013; 37, 2987
    Crossref