Skip to main content
SpringerLink
Log in

Alternative sources of syngas for hydroformylation of unsaturated compounds

  • Reviews
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Hydroformylation reactions and related tandem reactions (hydroformylation—hydrogenation, hydroaminomethylation) proceeding without introduction of syngas were considered. Reaction systems, in which other gases or liquid-dissolved reagents were used as a formyl group source, were described and systematized.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. P. Insard, B. Denise, R. P. A. Sneeden, J. Organomet. Chem., 1983, 256, 135.

    Google Scholar 

  2. Y. Wang, W. Ren, J. Li, H. Wang, Y. Shi, Org. Lett., 2014, 16, 5960.

    CAS  PubMed  Google Scholar 

  3. W. Ueda, T. Yokoyama, Y. Morikawa, Y. Moro-oka, T. Ikawa, J. Mol. Catal., 1988, 44, 197.

    CAS  Google Scholar 

  4. T. Kondo, T. Okada, T. Mitsudo, Organomet., 1999, 18, 4123.

    CAS  Google Scholar 

  5. S. Cacchi, G. Fabrizi, A. Goggiamani, Org. Lett., 2003, 5, 4269.

    CAS  PubMed  Google Scholar 

  6. S. Ko, C. Lee, M.-G. Choi, Y. Na, S. Chang, J. Org. Chem., 2003, 68, 1607.

    CAS  PubMed  Google Scholar 

  7. N.-F. K. Kaiser, A. Hallberg, M. Larhed, J. Combinator. Chem., 2002, 4, 109.

    CAS  Google Scholar 

  8. P. J. Tambade, Y. P. Patil, M. J. Bhanushali, B. M. Bhanage, Tetrahedron Lett., 2008, 49, 2221.

    CAS  Google Scholar 

  9. T. Morimoto, K. Kakiuchi, Angew. Chem., Int. Ed., 2004, 43, 5580.

    CAS  Google Scholar 

  10. L. Wu, Q. Liu, R. Jackstell, M. Beller, Angew. Chem., Int. Ed., 2014, 53, 6310.

    CAS  Google Scholar 

  11. W. Reppe, H. Vetter, Justus Liebigs Ann. Chem., 1953, 582, 133.

    CAS  Google Scholar 

  12. A. Ambrosi, E. Scott, Angew. Chem., Int. Ed., 2016, 55, 2.

    Google Scholar 

  13. H. Kang, C. H. Mauldin, T. Cole, W. Slegeir, K. Cann, R. Pettit, J. Am. Chem. Soc., 1977, 99, 8323.

    CAS  Google Scholar 

  14. K. Murata, A. Matsuda, Bull. Chem. Soc. Jpn, 1981, 54, 245.

    CAS  Google Scholar 

  15. K. Murata, A. Matsuda, K. Bando, Y. Sugi, J.C.S. Chem. Commun., 1979, No. 18, 785.

  16. R. M. Laine, Am. Chem. Soc., 1978, 100, 6451.

    CAS  Google Scholar 

  17. R. Vargas, A. B. Rivas, J. D. Suarez, I. Chaparros, M. C. Ortega, A. J. Pardey, C. Longo, J. J. Perez-Torrente, L. Oro, Catal. Lett., 2009, 130, 470.

    CAS  Google Scholar 

  18. A. J. Pardey, J. Brito, M. Fernandes, A. B. Rivas, M. S. Ortega, C. Longo, P. J. Barichelli, E. Lujano, S. A. Moya, React. Kinet. Catal. Lett., 74, 111.

  19. G. Fachinetti, T. Funaioli, F. Marchetti, Chem. Commun., 2005, 2912.

  20. M. M. Mdleleni, R. G. Rinker, P. C. Ford, Inorg. Chim. Acta, 1998, 270, 345.

    CAS  Google Scholar 

  21. J. Liu, K. Kubis, R. Franke, R. Jackstell, M. Beller, ACS Catal. 2016, 6, 907.

    CAS  Google Scholar 

  22. S. Gülak, L. Wu, Q. Liu, R. Franke, R. Jackstell, M. Beller, Angew. Chem., Int. Ed., 2014, 53, 7320.

    Google Scholar 

  23. K. Tominaga, Y. Sasaki, Catal. Commun., 2000, 1, 1.

    CAS  Google Scholar 

  24. S. Fujita, S. Okamura, Y. Akiyama, M. Arai, Int. J. Mol. Sci., 2007, 8, 749.

    CAS  PubMed Central  Google Scholar 

  25. S. Jääskeläinen, M. Haukka, Appl. Catal. A: General, 2003, 247, 95.

    Google Scholar 

  26. K. Tominaga, Y. Sasaki, Appl. Catal. A: General, 2004, 220, 159.

    CAS  Google Scholar 

  27. K. Tominaga, Y. Sasaki, Chem. Lett., 2004, 33, 14.

    CAS  Google Scholar 

  28. K. Tominaga, Catal. Today, 2006, 115, 70.

    CAS  Google Scholar 

  29. M.-L. Kontkanen, L. Oresmaa, M. A. Moreno, J. Jänis, E. Laurila, M. Haukka, Appl. Catal. A: General, 2009, 365, 130.

    CAS  Google Scholar 

  30. V. K. Srivastava, P. Eilbracht, Catal. Commun., 2009, 10, 1791.

    CAS  Google Scholar 

  31. S. J. Ahlers, M.-M. Pohl, M. Holena, D. Linke, E. V. Kondratenko, Catal. Sci. Technol., 2016, 6, 2171.

    CAS  Google Scholar 

  32. D. Heyl, C. Kreyenschulte, V. A. Kondratenko, U. Bentrup, E. V. Kondratenko, A. Brückner, ChemSusChem., 2019, 12, 651.

    CAS  PubMed  Google Scholar 

  33. M. G. Mura, L. De Luca, G. Giacomelli, A. Porcheddu, Adv. Synth. Catal., 2012, 354, 3180.

    CAS  Google Scholar 

  34. W. Ren, W. Chang, J. Dai, Y. Shi, J. Li, Y. Shi, J. Am. Chem. Soc., 2016, 138, 14864.

    CAS  PubMed  Google Scholar 

  35. P. Kalk, Y. Perez, J. Jenk, Adv. Organomet. Chem., 1991, 32, 121.

    Google Scholar 

  36. G. Jenner, E. M. Nahmed, S. Libs-Konrath, J. Mol. Catal., 1991, 64, 337.

    CAS  Google Scholar 

  37. G. Jenner, Tetrahedron Lett., 1991, 32, 505.

    CAS  Google Scholar 

  38. G. Jenner, Appl. Catal., 1991, 75, 289.

    CAS  Google Scholar 

  39. G. Jenner, A. Ben Taleb, J. Mol. Catal., 1994, 91, 31.

    CAS  Google Scholar 

  40. E. Karakhanov, A. Maksimov, Y. Kardasheva, E. Runova, R. Zakharov, M. Terenina, C. Kenneally, V. Arredondo, Catal. Sci. Technol., 2014, 4, 540.

    CAS  Google Scholar 

  41. T. Okano, T. Kobayashi, H. Konishi, J. Kiji, Tetrahedron Lett., 1982, 23, 4967.

    CAS  Google Scholar 

  42. H. S. Ahn, S. H. Han, S. J. Uhm, W. K. Seok, H. N. Lee, G. A. Korneeva, J. Mol. Catal. A: Chem., 1999, 144, 295.

    CAS  Google Scholar 

  43. M. Rosales, A. González, B. González, C. Moratinos, H. Pérez, J. Urdaneta, R. A. Sánchez-Delgado, J. Organomet. Chem., 2005, 690, 3095.

    CAS  Google Scholar 

  44. M. Rosales, F. Arrieta, P. Baricelli, A. González, B. González, Y. Guerrero, C. Moratinos, I. Pacheco, H. Pérez, J. Urdaneta, Catal. Lett., 2008, 126, 367.

    CAS  Google Scholar 

  45. G. Makado, T. Morimoto, Y. Sugimoto, K. Tsutsumi, N. Kagawa, K. Kakiuchi, Adv. Synth. Catal., 2010, 352, 299.

    CAS  Google Scholar 

  46. E. Cini, E. Airiau, N. Girard, A. Mann, J. Salvadori, M. Taddei, Synlett, 2011, No. 2, 199.

  47. H. Ren, W. D. Wulff, Org. Lett., 2013, 15, 242.

    CAS  PubMed  Google Scholar 

  48. M. Vilches-Herrera, M. Concha-Puelles, N. Carvajal, J. Molina, R. Santander, M. C. Rezende, S. Lühr, Catal. Commun., 2018, 116, 62.

    CAS  Google Scholar 

  49. T. Morimoto, T. Fujii, K. Miyoshi, G. Makado, H. Tanimoto, Y. Nishiyama, K. Kakiuchi, Org. Biomol. Chem., 2015, 13, 4632.

    CAS  PubMed  Google Scholar 

  50. J. A. Fuentes, R. Pittaway, M. L. Clarke, Chem. Eur. J., 2015, 21, 10645.

    CAS  PubMed  Google Scholar 

  51. M. Uhlemann, S. Doerfelt, A. Börner, Tetrahedron Lett., 2013, 54, 2209.

    CAS  Google Scholar 

  52. A. Kopfer, B. Sam, B. Breit, M. J. Krische, Chem. Sci., 2013, 4, 1876.

    Google Scholar 

  53. S. K. Murphy, J-W. Park, F. A. Cruz, V. M. Dong, Science, 2015, 347, 56.

    CAS  PubMed  PubMed Central  Google Scholar 

  54. E. P. K. Olsen, R. Madsen, Chem. Eur. J., 2012, 18, 16023.

    CAS  PubMed  Google Scholar 

  55. J. J. Verendel, M. Nordlund, P. G. Andersson, ChemSusChem., 2013, 6, 426.

    CAS  PubMed  Google Scholar 

  56. S. H. Christensen, E. P. K. Olsen, J. Rosenbaum, R. Madsen, Org. Biomol. Chem., 2015, 13, 938.

    CAS  PubMed  Google Scholar 

  57. Y. Yamada, C. K. Tsung, W. Huang, Z. Huo, S. E. Habas, T. Soejima, C. E. Aliaga, G. A. Somorjai, P. Yang, Nature Chem., 2011, 3, 372.

    CAS  Google Scholar 

  58. J. Su, C. Xie, C. Chen, Y. Yu, G. Kennedy, G. A. Somorjai, P. Yang, J. Am. Chem. Soc., 2016, 138, 11568.

    CAS  PubMed  Google Scholar 

  59. J. Moran, A. Preetz, R. A. Mesch, M. J. Krische, Nature Chem., 2011, 3, 287.

    CAS  Google Scholar 

  60. Y. Liu, L. Cai, S. Xu, W. Pu, X. Tao, Chem. Commun., 2018, 54, 2166.

    CAS  Google Scholar 

  61. H. Huang, C. Yu, Y. Zhang, Y. Zhang, P. S. Mariano, W. Wang, J. Am. Chem. Soc., 2017, 139, 9799.

    CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Lomonosov Moscow State University, Department of Chemistry, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    D. N. Gorbunov, M. V. Nenasheva, Yu. S. Kardasheva & E. A. Karakhanov

Authors
  1. D. N. Gorbunov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. V. Nenasheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. S. Kardasheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. A. Karakhanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to D. N. Gorbunov.

Additional information

This work was financially supported by the Russian Foundation for Basic Research (Project No. 18-33-01227).

Based on the materials of the 18th IUPAC International Symposium “Macromolecular Metal Complexes” (June 10–13, 2019, Tver, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0625–0634, April, 2020.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gorbunov, D.N., Nenasheva, M.V., Kardasheva, Y.S. et al. Alternative sources of syngas for hydroformylation of unsaturated compounds. Russ Chem Bull 69, 625–634 (2020). https://doi.org/10.1007/s11172-020-2810-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-020-2810-y

Key words

Search

Navigation