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 K. Joshi thanks the CSIR (Grant no. 01(2996)/19/EMR-II) for financial assistance.


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%.

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