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Self-Coupling of Secondary Alcohols and α-Alkylation of Methyl Ketones with Secondary Alcohols by Pt/CeO2 Catalyst

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Abstract

Transition metal-loaded metal oxides are tested for C–C self-coupling of 2-octanol to a higher ketone at 140 °C. Among various catalysts, Pt/CeO2 shows the highest activity and shows good reusability. Pt/CeO2 is effective for the self-coupling of various aliphatic secondary alcohols and α-alkylation of methyl ketones with aliphatic secondary alcohols. A possible reaction mechanism is discussed.

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References

  1. Hamid MHSA, Slatford PA, Williams JMJ (2007) Adv Synth Catal 349:1555

    Article  CAS  Google Scholar 

  2. Guillena G, Ramón DJ, Yus M (2007) Angew Chem Int Ed 46:2358

    Article  CAS  Google Scholar 

  3. Taguchi K, Nakagawa H, Hirabayashi T, Sakaguchi S, Ishii Y (2004) J Am Chem Soc 126:72

    Article  CAS  Google Scholar 

  4. Cho CS, Kim BT, Kim T-J, Shim SC (2001) J Org Chem 66:9020

    Article  CAS  Google Scholar 

  5. Martinez R, Brand G-J, Ramon D-J, Yus M (2005) Tetrahedron Lett 46:3683

    Article  CAS  Google Scholar 

  6. Kuwahara T, Fukuyama T, Ryu I (2012) Org Lett 14:4703

    Article  CAS  Google Scholar 

  7. Cho CS (2005) J Mol Catal A 240:55

    CAS  Google Scholar 

  8. Kwon MS, Kim N, Seo SH, Park IS, Cheedrala RK, Park J (2005) Angew Chem Int Ed 44:6913

    Article  CAS  Google Scholar 

  9. Yamada YMA, Uozumi Y (2006) Org Lett 8:1375

    Article  CAS  Google Scholar 

  10. Kim S, Bae SW, Lee JS, Park J (2009) Tetrahedron 65:1461

    Article  CAS  Google Scholar 

  11. Alonso F, Riente P, Yus M (2011) Acc Chem Res 44:379

    Article  CAS  Google Scholar 

  12. Cho CS, Kim BT, Kim HS, Kim TJ, Shim SC (2003) Organometallics 22:3608

    Article  CAS  Google Scholar 

  13. Martinez R, Ramón DJ, Yus M (2006) Tetrahedron 62:8982

    Article  CAS  Google Scholar 

  14. Viciano M, Sanau M, Peris E (2007) Organometallics 26:6050

    Article  CAS  Google Scholar 

  15. Prades A, Viciano M, Sanau M, Peris E (2008) Organometallics 27:4254

    Article  CAS  Google Scholar 

  16. Chang X, Chuan LW, Yongxin L, Pullarkat SA (2012) Tetrahedron Lett 53:1450

    Article  CAS  Google Scholar 

  17. Adair GRA, Williams JMJ (2005) Tetrahedron Lett 46:8233

    Article  CAS  Google Scholar 

  18. Cheung HW, Lee TY, Lui HY, Yeung CH, Lau CP (2008) Adv Synth Catal 350:2975

    Article  CAS  Google Scholar 

  19. Gnanamgari D, Leung CH, Schley ND, Hilton ST, Crabtree RH (2008) Org Biomol Chem 6:4442

    Article  CAS  Google Scholar 

  20. Gnanamgari D, Sauer ELO, Schley ND, Butler C, Incarvito CD, Crabtree RH (2009) Organometallics 28:321

    Article  CAS  Google Scholar 

  21. Fujita K, Asai C, Yamaguchi T, Hanasaka F, Yamaguchi R (2005) Org Lett 7:4017

    Article  CAS  Google Scholar 

  22. da Costa AP, Viciano M, Sanaú M, Merino S, Tejeda J, Peris E, Royo B (2008) Organometallics 27:1305

    Article  Google Scholar 

  23. da Costa AP, Sanau M, Peris E, Royo B (2009) Dalton Trans 38:6960

    Article  Google Scholar 

  24. Gong X, Zhang H, Li X (2011) Tetrahedron Lett 52:5596

    Article  CAS  Google Scholar 

  25. Xu C, Goh LY, Pullarkat SA (2011) Organometallics 30:6499

    Article  CAS  Google Scholar 

  26. Matsu-ura T, Sakaguchi S, Obora Y, Ishii Y (2006) J Org Chem 71:8306

    Article  CAS  Google Scholar 

  27. Koda K, Matsu-ura T, Obora Y, Ishii Y (2009) Chem Lett 38:838

    Article  CAS  Google Scholar 

  28. Obora Y, Anno Y, Okamoto R, Matsu-ura T, Ishii Y (2011) Angew Chem Int Ed 50:8618

    Article  CAS  Google Scholar 

  29. Kose O, Saito S (2010) Org Biomol Chem 8:896

    Article  CAS  Google Scholar 

  30. Carlini C, Girolamo MD, Macinai A, Marchionna M, Noviello M, Galletti AMR, Sbrana G (2003) J Mol Catal A 204–205:721

    Article  Google Scholar 

  31. Carlini C, Macinai A, Galletti AMR, Sbrana G (2004) J Mol Catal A 212:65

    Article  CAS  Google Scholar 

  32. Miura T, Kose O, Li F, Kai S, Saito S (2011) Chem Eur J 17:11146

    Article  CAS  Google Scholar 

  33. Liao S, Yu K, Li Q, Tian H, Zhang Z, Yu X, Xu Q (2012) Org Biomol Chem 10:2973

    Article  CAS  Google Scholar 

  34. Tang G, Cheng CH (2011) Adv Synth Catal 353:1918

    Article  CAS  Google Scholar 

  35. Yang J, Liu X, Meng DL, Chen HY, Zong ZH, Feng TT, Sun K (2012) Adv Synth Catal 354:328

    Article  CAS  Google Scholar 

  36. Cho CS, Ren WX, Shim SC (2005) Bull Korean Chem Soc 26:1611

    Article  CAS  Google Scholar 

  37. Cano R, Yus M, Ramón DJ (2012) Chem Commun 48:7628

    Article  CAS  Google Scholar 

  38. Shimizu K, Sato R, Satsuma A (2009) Angew Chem Int Ed 48:3982

    Article  CAS  Google Scholar 

  39. Carlini C, Girolamo MD, Marchionna M, Noviello M, Galletti AMR, Sbrana G (2002) J Mol Catal A 184:273

    Article  CAS  Google Scholar 

  40. Carlini C, Girolamo MD, Macinai A, Marchionna M, Noviello M, Galletti AMR, Sbrana G (2003) J Mol Catal A 200:137

    Article  CAS  Google Scholar 

  41. Cosimo JID, Torres G, Apesteguia CR (2002) J Catal 208:114

    Article  Google Scholar 

  42. El-Molla SA (2006) Appl Catal A 298:103

    Article  CAS  Google Scholar 

  43. Torres G, Apesteguia CR, Cosimo JID (2007) Appl Catal A 317:161

    Article  CAS  Google Scholar 

  44. Carlini C, Macinai A, Marchionna M, Noviello M, Galletti AMR, Sbrana G (2003) J Mol Catal A 206:409

    Article  CAS  Google Scholar 

  45. Carlini C, Marchionna M, Noviello M, Galletti AMR, Sbranaa G, Basiled F, Vaccarid A (2005) J Mol Catal A 232:13

    Article  CAS  Google Scholar 

  46. Cosimo JID, Apesteguia CR, Gines MJL, Iglesia E (2000) J Catal 190:261

    Article  Google Scholar 

  47. Ndou AS, Plint N, Coville NJ (2003) Appl Catal A 251:337

    Article  CAS  Google Scholar 

  48. Ndou AS, Coville NJ (2004) Appl Catal A 275:103

    Article  CAS  Google Scholar 

  49. Tsuchida T, Sakuma S, Takeguchi T, Ueda W (2006) Ind Eng Chem Res 45:8634

    Article  CAS  Google Scholar 

  50. Tsuchida T, Kubo J, Yoshioka T, Sakuma S, Takeguchi T, Ueda W (2008) J Catal 259:183

    Article  CAS  Google Scholar 

  51. Ogo S, Onda A, Yanagisawa K (2011) Appl Catal A 402:188

    Article  CAS  Google Scholar 

  52. Ogo S, Onda A, Iwasa Y, Hara K, Fukuoka A, Yanagisawa K (2012) J Catal 296:24

    Article  CAS  Google Scholar 

  53. Leon M, Diaz E, Ordonez S (2011) Catal Today 164:436

    Article  CAS  Google Scholar 

  54. Leon M, Diaz E, Vega A, Ordonez S, Auroux A (2011) Appl Catal B 102:590

    Article  CAS  Google Scholar 

  55. Shimura K, Kon K, Siddiki SMAH, Shimizu K (2013) Appl Catal A 462:137

    Article  Google Scholar 

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Acknowledgments

This work was supported by a MEXT program “Elements Strategy Initiative to Form Core Research Center” (since 2012), Japan.

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Correspondence to Ken-ichi Shimizu.

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Chaudhari, C., Siddiki, S.M.A.H. & Shimizu, Ki. Self-Coupling of Secondary Alcohols and α-Alkylation of Methyl Ketones with Secondary Alcohols by Pt/CeO2 Catalyst. Top Catal 57, 1042–1048 (2014). https://doi.org/10.1007/s11244-014-0268-6

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  • DOI: https://doi.org/10.1007/s11244-014-0268-6

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