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Synthesis, Characterization and Biomimetic Activity of Heterogenized Dioxidomolybdenum(VI) Complex and Its Homogeneous Analogue

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Abstract

Cis-[MoVIO2(CH3-hptb)(MeOH)] (1) has been synthesized by the reaction of [MoVIO2(acac)2] and deferasirox [ICL670: 4-[3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoic acid, H3hptb, I] in 1:1 molar ratio in MeOH. Complex 1 has been characterized successfully by several spectral techniques, viz. FT-IR, UV–Vis, 1H and 13C NMR, elemental (CHN) and thermogravimetric analysis. The esterification of the carboxylic group of ligand was observed during the complexation process with molybdenum. The analogous heterogeneous complex [MoVIO2(hptb)(MeOH)]@APTMS-TiO2 (2) has been synthesized by immobilizing I on amine-functionalized TiO2, {[H2hptb]@APTMS-TiO2 (II)} and then reacting it with [MoVIO2(acac)2] in MeOH. Characterization of the immobilized complex was achieved through FT-IR, DRS, P-XRD, TEM, thermogravimetric analysis and MP-AES. Both the complexes have been utilized in synthesizing organobromine compounds through oxidative bromination of styrene in the presence of KBr, oxidant (30% aq. H2O2) and 70% aq. HClO4 at room temperature. With the formation of 2-bromo-1-phenylethane-1-ol and 1-phenylethane-1,2-diol under the optimized reaction conditions, 72 and 100% conversion of styrene was achieved in the presence of catalysts 1 and 2, respectively. The oxidative bromination of thymol with catalyst 2 provides 2-bromothymol (52%) and 2,4-dibromothymol (48%) with 100% conversion.

Graphical Abstract

Dioxidomolybdenum(VI) complex of ICL670 immobilized on amine-functionalized titania has been synthesized and used as a functional model of haloperoxidases for the oxidative bromination of thymol and styrene.

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References

  1. Dagani MJ, Barda HJ, Benya TJ, Sanders DC (2000) Bromine compounds. Ullmann’s encyclopedia of industrial chemistry

  2. House H (1972) Modern Synthetic Reactions, 2nd edn p. 383

  3. De Meijere A, Diederich F (2004) Metal-catalyzed cross-coupling reactions. Wiley, New York, pp 70–86

    Book  Google Scholar 

  4. Lodder G, Cornelisse J, Patai S, Rappoport Z (1995) The Chemistry of Functional Groups, Supplement D2

  5. Turner DL (1972) J Food Sci 37:791–792

    Article  CAS  Google Scholar 

  6. Laskowski DA (2002) Rev Environ Contam Toxicol 74:49–170

    Article  Google Scholar 

  7. Wanière GH (1973) In: Patai S (ed.) The chemistry of functional groups—the chemistry of the carbon-halogen bond. Wiley, Chichester

  8. Green J (1996) J Fire Sci 14:426–442

    Article  CAS  Google Scholar 

  9. Gribble GW (1999) Chem Soc Rev 28:335–346

    Article  CAS  Google Scholar 

  10. Friedländer P (1909) Ber Dtsch Chem Ges 42:765–770. https://doi.org/10.1002/cber.190904201122

    Article  Google Scholar 

  11. Smith MB, March J (2007) March’s advanced organic chemistry: reactions, mechanisms, and structure, 6th edn. John Wiley & Sons Inc, Hodoken, New Jersey

    Google Scholar 

  12. Kogel JE, Trivedi NC, Barker JM, Krukowski ST (2006) Industrial minerals & rocks: commodities, markets and uses, 7th edn. Society for mining, metallurgy and exploration, (SME) 285–294

  13. Carrenõ MC, Ruano JLG, Sanz G, Toledo MA, Urbano A (1995) J Org Chem 60:5328–5331

    Article  Google Scholar 

  14. Oberhauser T (1997) J Org Chem 62:4504–4506

    Article  CAS  PubMed  Google Scholar 

  15. Rajagopal R, Jarikote DV, Lahoti RJ, Daniel T, Srinivasan KV (2003) Tetrahedron Lett 44:1815–1817

    Article  CAS  Google Scholar 

  16. Sarma JARP, Nagaraju A (2000) J Chem Soc Perkin Trans 2(6):1113–1118

    Article  Google Scholar 

  17. Pravst I, Zupan M, Stavber S (2006) Green Chem 8:1001–1005

    Article  CAS  Google Scholar 

  18. Heropoulos GA, Cravotto G, Screttas CG, Steele BR (2007) Tetrahedron Lett 48:3247–3250

    Article  CAS  Google Scholar 

  19. Pravst I, Zupan M, Stavber S (2008) Tetrahedron 64:5191–5199

    Article  CAS  Google Scholar 

  20. Chiappe C, Leandri E, Pieraccini D (2004) Chem Commun 2004(22):2536–2537

    Article  Google Scholar 

  21. Kavala V, Naik S, Patel BK (2005) J Org Chem 70:4267–4271

    Article  CAS  PubMed  Google Scholar 

  22. Salazar J, Dorta R (2004) Synlett 2004:1318–1320

    Article  Google Scholar 

  23. Fu H, Kondo H, Ichikawa Y, Look GC, Wong CH (1992) J Org Chem 57:7265–7270

    Article  CAS  Google Scholar 

  24. Tenaglia A, Pardigon O, Buono G (1996) J Org Chem 61:1129–1132

    Article  CAS  Google Scholar 

  25. Majetich G, Hicks R, Reister S (1997) J Org Chem 62:4321–4326

    Article  CAS  PubMed  Google Scholar 

  26. Eissen M, Lenoir D (2008) Chem Eur J 14:9830–9841

    Article  CAS  PubMed  Google Scholar 

  27. Podgoršek A, Zupan M, Iskra J (2009) Angew Chem Intl Edn 48:8424–8450

    Article  Google Scholar 

  28. Anastas PT, Warner JC (1998) Green chemistry: theory and practice. Oxford University Press, Oxford, London

    Google Scholar 

  29. Sheldon RA (2000) Green Chem 2:G1–G4

    Article  Google Scholar 

  30. Anastas PT, Bartlett LB, Kirchhoff MM, Williamson TC (2000) Catal today 55:11–22

    Article  CAS  Google Scholar 

  31. Conte V, Di Furia F, Moro S (1994) Tetrahedron Lett 35:7429–7432

    Article  CAS  Google Scholar 

  32. Sels BF, De Vos DE, Jacobs PA (2001) J Am Chem Soc 123:8350–8359

    Article  CAS  PubMed  Google Scholar 

  33. Moriuchi T, Yamaguchi M, Kikushima K, Hirao T (2007) Tetrahedron Lett 48:2667–2670

    Article  CAS  Google Scholar 

  34. Rothenberg G, Clark JH (2000) Org Process Res Dev 4:270–274

    Article  CAS  Google Scholar 

  35. Choudary BM, Sudha Y, Reddy PN (1994) Synlett 1994:450

    Article  Google Scholar 

  36. Firouzabadi H, Iranpoor N, Kazemi S, Ghaderi A, Garzan A (2009) Adv Synth Catal 351:1925–1932

    Article  CAS  Google Scholar 

  37. Mallik S, Parida KM, Dash SS (2007) J Mol Catal A: Chem 261:172–179

    Article  CAS  Google Scholar 

  38. Mallik S, Parida KM (2007) Catal Commun 8:889–893

    Article  Google Scholar 

  39. Van Pee KH, Unversucht S (2003) Chemosphere 52:299–312

    Article  PubMed  Google Scholar 

  40. Meister GE, Butler A (1994) Inorg Chem 33:3269–3275

    Article  CAS  Google Scholar 

  41. Reynolds MS, Morandi SJ, Raebiger JW, Melican SP, Smith SPE (1994) Inorg Chem 33:4977–4984

    Article  CAS  Google Scholar 

  42. Boruah JJ, Das SP, Borah R, Gogoi SR, Islam NS (2013) Polyhedron 52:246–254

    Article  CAS  Google Scholar 

  43. Bora U, Chaudhuri MK, Dey D, Dhar SS (2001) Pure Appl Chem 73:93–102

    Article  CAS  Google Scholar 

  44. Olowoyo JO, Hernández NC, Kumar M, Jain SL, Babalola JO, Kumar U (2018) ChemistrySelect 3:3659–3663

    Article  CAS  Google Scholar 

  45. Sarkheil M, Lashanizadegan M, Ghiasi M (2019) J Mol Str 1179:278–288

    Article  CAS  Google Scholar 

  46. Chen GJJ, McDonald JW, Newton WE (1976) Inorg Chem 15:2612–2615

    Article  CAS  Google Scholar 

  47. Steinhauser S, Heinz U, Bartholomä M, Weyhermüller T, Nick H, Hegetschweiler K (2004) Eur J Inorg Chem 2004(21):4177–4192

    Article  Google Scholar 

  48. Maurya MR, Saini N, Avecilla F (2015) RSC Adv 5:101076–101088

    Article  CAS  Google Scholar 

  49. Maurya MR, Chauhan A, Arora S, Gupta P (2022) Catal Today 397–399:3–15

    Article  Google Scholar 

  50. Maurya MR, Sarkar B, Avecilla F, Tariq S, Azam A, Correia I (2016) Eur J Inorg Chem 2016(9):1430–1441

    Article  CAS  Google Scholar 

  51. Maurya MR, Chauhan A, Verma A, Kumar U, Avecilla F (2020) Catal Today 388–389:274–287

    Google Scholar 

  52. Shang X, Li B, Li C, Wang X, Zhang T, Jiang S (2013) Dyes Pigm 98:358–366

    Article  CAS  Google Scholar 

  53. Di Paola A, Marci G, Palmisano L, Schiavello M, Uosaki K, Ikeda S, Ohtani B (2002) J Phys Chem B 106:637–645

    Article  Google Scholar 

  54. Maurya MR, Dhaka S, Avecilla F (2014) Polyhedron 67:145–159

    Article  CAS  Google Scholar 

  55. Maurya MR, Mengesha B, Maurya SK, Sehrawat N, Avecilla F (2019) Inorg Chim Acta 486:757–765

    Article  CAS  Google Scholar 

  56. Conte V, Coletti A, Floris B, Licini G, Zonta C (2011) Coord Chem Rev 255:2165–2177

    Article  CAS  Google Scholar 

  57. Maurya MR, Haldar C, Khan AA, Azam A, Salahuddin A, Kumar A, Costa Pessoa J (2012) Eur J Inorg Chem 2012(15):2560–2577

    Article  CAS  Google Scholar 

  58. Maurya MR, Maurya SK, Kumar N, Gupta P (2021) Eur J Inorg Chem 2021(27):2724–2738

    Article  CAS  Google Scholar 

  59. Mohanty M, Maurya SK, Banerjee A, Patra SA, Maurya MR, Crochet A, Brzezinski K, Dinda R (2019) New J Chem 43:17680–17695

    Article  CAS  Google Scholar 

  60. Kurapati SK, Maloth S, Pal S (2015) Inorg Chim Acta 430:66–73

    Article  CAS  Google Scholar 

  61. Biswal D, Pramanik NR, Chakrabarti S, Drew MG, Sarkar B, Maurya MR, Mukherjee SK, Chowdhury P (2017) New J Chem 41:4116–4137

    Article  CAS  Google Scholar 

  62. Maurya MR, Mengesha B, Maurya SK, Avecilla F (2019) Inorg Chim Acta 493:118–126

    Article  CAS  Google Scholar 

  63. Kurapati SK, Pal S (2016) Appl Organomet Chem 30:116–124

    Article  CAS  Google Scholar 

  64. Ghosh S, Kurapati SK, Pal S (2017) Polyhedron 125:26–33

    Article  CAS  Google Scholar 

  65. Kesharwani N, Chaudhary N, Haldar C (2021) Catal Lett 151:3562–3581

    Article  CAS  Google Scholar 

  66. Maurya MR, Rana L, Avecilla F (2016) Inorg Chim Acta 440:172–180

    Article  CAS  Google Scholar 

  67. Maurya MR, Dhaka S, Avecilla F (2015) Polyhedron 96:79–87

    Article  CAS  Google Scholar 

  68. Maurya MR, Uprety B, Avecilla F, Adão P, Pessoa JC (2015) Dalton Trans 44:17736–17755

    Article  CAS  PubMed  Google Scholar 

  69. Maurya MR, Jangra N, Avecilla F, Correia I (2019) Eur J Inorg Chem 2019(2):314–329

    Article  CAS  Google Scholar 

  70. Maurya MR, Kumar A, Ebel M, Rehder D (2006) Inorg Chem 45:5924–5937

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

MRM thanks the Science and Engineering Research Board (SERB), Department of Science and Technology, Government of India, New Delhi, India for financial support of the work (Grant Number CRG/2018/000182). AC is thankful to University Grant Commission, New Delhi, India for Senior Research Fellowship.

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  1. Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, 247 667, India

    Mannar R. Maurya & Abhilasha Chauhan

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Maurya, M.R., Chauhan, A. Synthesis, Characterization and Biomimetic Activity of Heterogenized Dioxidomolybdenum(VI) Complex and Its Homogeneous Analogue. Top Catal 66, 420–434 (2023). https://doi.org/10.1007/s11244-022-01747-7

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