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Synthesis, Characterization and Catalytic Activity of a Tungsten(VI) Amino Triphenolate Complex

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Abstract

Synthesis, characterization and catalytic activity of a novel tungsten(VI) amino triphenolate complex have been investigated. In particular, a tungsten(VI) amino triphenolate complex has been synthesized and tested in the oxidation of sulfides and cyclooctene, using hydrogen peroxide as terminal oxidant. The catalyst has proved to be air and water tolerant, also showing a good efficiency in terms of yields and selectivity. Moreover, an upgrade of our previous ligand synthesis is herein reported. The new developed procedure allows to obtain the triphenolamine in large scale without the use of chromatography for the intermediates purification.

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References

  1. Mugdan M, Young DP (1949) J Chem Soc 2988

  2. Prandi J, Kagan HB, Mimoun H (1986) Tetrahedron Lett 23:2617

    Article  Google Scholar 

  3. Venturello C, Alneri E, Ricci M (1983) J Org Chem 48:3831

    Article  CAS  Google Scholar 

  4. Kirshenbaum KS, Sharpless KB (1985) J Org Chem 50:1979

    Article  CAS  Google Scholar 

  5. De Vos DE, Sels BF, Jacobs PA (2002) Adv Catal 46:1

    Google Scholar 

  6. Weinstock IA, Barbuzzi EMG, Wemple MW, Cowan JJ, Reiner RS, Sonnen DM, Heintz RA, Bond JS, Hill CL (2001) Nature 414:191

    Article  CAS  Google Scholar 

  7. Ichihara J (2001) Tetrahedron Lett 42:695

    Article  CAS  Google Scholar 

  8. Hoegaerts D, Sels BF, de Vos DE, Verpoort F, Jacobs PA (2000) Catal Today 60:209

    Article  CAS  Google Scholar 

  9. Thiel WR, Eppinger J (1997) Chem Eur J, 696

  10. White MC, Doyle AG, Jacobsen EN (2001) J Am Chem Soc 123:7194

    Article  CAS  Google Scholar 

  11. Venturello G, Alneri E, Ricci M (1983) J Org Chem 48:3831

    Article  CAS  Google Scholar 

  12. Sato K, Aoki M, Ogawa M, Hashimoto T, Noyori R (1996) J Org Chem 61:8310

    Article  CAS  Google Scholar 

  13. Sato K, Aoki M, Ogawa M, Hashimoto T, Panyella D, Noyori R (1997) Bull Chem Soc Jpn 70:905

    Article  CAS  Google Scholar 

  14. Sato K, Aoki M, Noyori R (1998) Science 281:1646

    Article  CAS  Google Scholar 

  15. Sato K, Aoki M, Ogowa M, Hasimoto T, Noyori R (1996) J Org Chem 61:8310

    Article  CAS  Google Scholar 

  16. Sato K, Aoki M, Ogowa M, Hashimoto T, Panyela D, Noyori R (1997) Bull Chem Soc Jpn 70:905

    Article  CAS  Google Scholar 

  17. Kamata K, Yonehara K, Sumida Y, Yamaguchi M, Hikichi S, Mizuno N (2003) Science 300:964

    Article  CAS  Google Scholar 

  18. Aminia M, Mehdi Haghdoost M, Bagherzadeh M (2014) Coord Chem Rev 268:83

    Article  Google Scholar 

  19. Dinoi C, Ciclosi M, Manoury E, Maron L, Perrin L, Poli R (2010) Chem Eur J 16:9572

    Article  CAS  Google Scholar 

  20. Dinoi C, Poli R, Perrin L, Maron L (2012) Dalton Trans 41:1131

    Article  CAS  Google Scholar 

  21. Vrdoljak V, Pisk J, Agustin D, Novak P, Parlov Vuković J, Matković-Čalogović D (2014) New J Chem 38:6176

    Article  CAS  Google Scholar 

  22. Vrdoljak V, Pisk J, Prugovečki B, Agustin D, Novak P, Matković-Čalogović D (2016) RSC Adv 6:36384

    Article  CAS  Google Scholar 

  23. Chmura AJ, Davidson MG, Frankis CJ, Jones MD, Lunn MD (2008) Chem Commun. doi:10.1039/b718678a

    Google Scholar 

  24. Gendler S, Segal S, Goldberg I, Goldschmidt Z, Kol M (2006) Inorg Chem 45:4783

    Article  CAS  Google Scholar 

  25. Peuronen A, Lehtonen A (2016) Top Catal 59:1132

    Article  CAS  Google Scholar 

  26. Di Furia F, Licini G, Modena G, Motterle R (1996) J Org Chem 61:5175

    Article  CAS  Google Scholar 

  27. Bonchio M, Licini G, Modena G, Moro S, Bortolini O, Traldi P, Nugent WA (1997) Chem Commun. doi:10.1039/A701227F

    Google Scholar 

  28. Bonchio M, Calloni S, Di Furia F, Licini G, Modena G, Moro S, Nugent WA (1997) J Am Chem Soc 119:6935

    Article  CAS  Google Scholar 

  29. Licini G, Bonchio M, Modena G, Nugent WA (1999) Pure Appl Chem 71:463

    Article  CAS  Google Scholar 

  30. Favretto L, Nugent WA, Licini G (2002) Tetrahedron Lett 43:2581

    Article  CAS  Google Scholar 

  31. Santoni G, Mba M, Bonchio M, Nugent WA, Zonta C, Licini G (2010) Chem Eur J 16:645

    Article  CAS  Google Scholar 

  32. Scaramuzzo FA, Licini G, Zonta C (2013) Chem Eur J 19:16809

    Article  CAS  Google Scholar 

  33. Badetti E, Wurst K, Licini G, Zonta C (2016) Chem Eur J 22:6515

    Article  CAS  Google Scholar 

  34. Berardozzi R, Badetti E, Carmo Dos Santos NA, Wurst K, Licini G, Pescitelli G, Zonta C, Di Bari L (2016) Chem Comm 52:8428

    Article  CAS  Google Scholar 

  35. Natali M, Badetti E, Deponti E, Gamberoni M, Scaramuzzo FA, Sartorel A, Zonta C (2016) Dalton Trans 45:14764

    Article  CAS  Google Scholar 

  36. Scaramuzzo FA, Badetti E, Licini G, Zonta C (2017) Eur J Org Chem 11:1438

    Article  Google Scholar 

  37. Bravin C, Badetti E, Scaramuzzo FA, Licini G, Zonta C (2017) J Am Chem Soc 139:6456

    Article  CAS  Google Scholar 

  38. Mba M, Pontini M, Lovat S, Zonta C, Bernardinelli G, Kündig EP, Licini GM (2008) Inorg Chem 47:8616

    Article  CAS  Google Scholar 

  39. Zonta C, Cazzola E, Mba M, Licini G (2008) Adv Synth Catal 350:2503

    Article  CAS  Google Scholar 

  40. Licini G, Mba M, Zonta C (2009) Dalton Trans. doi:10.1039/b822653a

    Google Scholar 

  41. Mba M, Prins LJ, Zonta C, Cametti M, Valkonen A, Rissanen K, Licini G (2010) Dalton Trans 39:7384

    Article  CAS  Google Scholar 

  42. Romano F, Linden A, Mba M, Zonta C, Licini G (2010) Adv Synth Catal 352:2937

    Article  CAS  Google Scholar 

  43. Zonta C, Kolarovic A, Mba M, Pontini M, Kündig EP, Licini G (2011) Chirality 23:796

    Article  CAS  Google Scholar 

  44. Whiteoak CJ, Gjoka B, Martin E, Martínez Belmonte M, Escudero-Adán EC, Zonta C, Licini G, Kleij AW (2012) Inorg Chem 51:10639

    Article  CAS  Google Scholar 

  45. Zonta C, Licini G (2013) Chem Eur J 19:9438

    Article  CAS  Google Scholar 

  46. Badetti E, Gjoka B, Nagy EM, Bernardinelli G, Kündig PE, Zonta C, Licini G (2015) Eur J Inorg Chem 21:3478

    Article  Google Scholar 

  47. Badetti E, Romano F, Marchiò L, Taşkesenlioǧlu S, Daştan A, Zonta C, Licini G (2016) Dalton Trans 45:14603

    Article  CAS  Google Scholar 

  48. Badetti E, Lloveras V, Romano F, Di Lorenzo R, Veciana J, Vidal-Gancedo J, Zonta C, Licini G (2016) Eur J Inorg Chem. doi:10.1002/ejic.201670311

    Google Scholar 

  49. Miceli C, Rintjema J, Martin E, Escudero-Adán EC, Zonta C, Licini G, Kleij AW (2017) ACS Catal 7:2367

    Article  CAS  Google Scholar 

  50. Prins LJ, Mba Blázquez M, Kolarović A, Licini G (2006) Tetrahedron Lett 47:2735

    Article  CAS  Google Scholar 

  51. Hänninen MM, Sillanpää R, Kiveläb H, Lehtonen A (2011) Dalton Trans 40:2868

    Article  Google Scholar 

  52. Lehtonen A, Sillanpää R (2005) Organometallics 24:2795

    Article  CAS  Google Scholar 

  53. Lehtonen A, Sillanpää R (2004) Inorg Chem 43:6501

    Article  CAS  Google Scholar 

  54. Dupé A, Hossain K, Schachner JA, Belaj F, Lehtonen A, Nordlander E, Mösch-Zanetti NC (2015) Eur J Inorg Chem 21:3572

    Article  Google Scholar 

  55. Ueyama N, Oku H, Kondo M, Okamura T, Yoshinaga N, Nakamura A (1996) Inorg Chem 35:643

    Article  CAS  Google Scholar 

  56. Sözen-Aktaş P, Manoury E, Demirhan F, Poli R (2013) Eur J Inorg Chem 15:2728

    Article  Google Scholar 

  57. Amarante TR, Antunes MM, Valente AA, Almeida Paz FA, Pillinger M, Gonçalves IS (2015) Inorg Chem 54:9690

    Article  CAS  Google Scholar 

  58. Bhaumik C, Manoury E, Daran JC, Sözen-Aktaş P, Demirhan F, Poli R (2014) J Organomet Chem 760:115

    Article  CAS  Google Scholar 

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Acknowledgements

This research was supported by Università di Padova (PRAT- CPDA153122) and Cariparo Foundation (F.R. fellowship). The project has been carried out in the frame of Cost Action CM1402—Crystallize.

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Correspondence to Cristiano Zonta or Giulia Licini.

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Badetti, E., Bonetto, A., Romano, F. et al. Synthesis, Characterization and Catalytic Activity of a Tungsten(VI) Amino Triphenolate Complex. Catal Lett 147, 2313–2318 (2017). https://doi.org/10.1007/s10562-017-2144-z

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  • DOI: https://doi.org/10.1007/s10562-017-2144-z

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