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Synthesis, Crystal Structures and their Utilities in Tishchenko Reaction of N,O-Bidentate Aluminum Compounds

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Abstract

Deprotonolysis of the N,O-bidentate pyridyl functionalized alkoxy ligands, 1,1-dimethyl-2-(pyridin-2-yl)ethanol (L 1H), 1-phenyl-2-(pyridin-2-yl)ethanol (L 2H) and 1,1-diphenyl-2-(pyridin-2-yl)ethanol (L 3H), with 1 equiv of AlMe3 gave the corresponding dimeric metal-monoalkyl compounds [L 1AlMe2]2 (1), [L 2AlMe2]2 (2), and [L 3AlMe2]2 (3), respectively. Compounds 1–3 were characterized by 1H and 13C NMR spectroscopy analysis, and the molecular structures of 1 and 2 were further confirmed by X-ray diffraction analysis. In the presence of iPrOH, aluminum compounds 1–2 exhibited excellent catalytic activity for the solvent-free Tishchenko reaction under mild conditions. In addition, the catalyst 3 can be easily isolated and recycled three times without a significant decrease in activity.

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Scheme 1
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References

  1. B. M. Trost (1991). Science 254, 1471.

    Article  CAS  Google Scholar 

  2. B. M. Trost (1995). Angew. Chem. 107, 285.

    Article  Google Scholar 

  3. B. M. Trost (1995). Angew. Chem. Int. Ed. Engl. 34, 259.

    Article  CAS  Google Scholar 

  4. R. A. Sheldon (2008). Chem. Commun. 29, 3352.

    Article  Google Scholar 

  5. L. Claisen (1887). Ber. 20, 646.

    Article  Google Scholar 

  6. W. Tischtschenko (1906). J. Russ. Phys. Chem. 38, 355.

    Google Scholar 

  7. M. O. Simon and S. Darses (2010). Adv. Synth. Catal. 352, 305.

    Article  CAS  Google Scholar 

  8. M. R. Crimmin, A. G. M. Barrett, M. S. Hill, and P. A. Procopiou (2007). Org. Lett. 9, 331.

    Article  CAS  Google Scholar 

  9. L. Cronin, F. Manoni, C. J. O’Connor, and S. J. Connon (2010). Angew. Chem. Int. Ed. 49, 3045.

    Article  CAS  Google Scholar 

  10. S. P. Curran and S. J. Connon (2012). Angew. Chem. Int. Ed. 51, 10866.

    Article  CAS  Google Scholar 

  11. T. Seki, T. Nakajo, and M. Onaka (2006). Chem. Lett. 35, 824.

    Article  CAS  Google Scholar 

  12. A. Zuyls, P. W. Roesky, G. B. Deacon, K. Konstas, and P. C. Junk (2008). Eur. J. Org. Chem. 2008, 693.

    Article  Google Scholar 

  13. S. Onozawa, T. Sakakura, M. Tanaka, and M. Shiro (1996). Tetrahedron 52, 4291.

    Article  CAS  Google Scholar 

  14. T. Andrea, E. Barnea, and M. S. Eisen (2008). J. Am. Chem. Soc. 130, 2454.

    Article  CAS  Google Scholar 

  15. W. I. Dzik and L. J. Gooβen (2011). Angew. Chem. Int. Ed. 50, 11047.

    Article  CAS  Google Scholar 

  16. C. Tejel, M. A. Ciriano, and V. Passarelli (2011). Chem. Eur. J. 17, 91.

    Article  CAS  Google Scholar 

  17. K. I. Morita, Y. Nishiyama, and Y. Ishii (1993). Organometallics 12, 3748.

    Article  CAS  Google Scholar 

  18. T. Ito, H. Horino, Y. Koshiro, and A. Yamamoto (1982). Bull. Chem. Soc. Jpn. 55, 504.

    Article  CAS  Google Scholar 

  19. M. Yamashita and T. Ohishi (1993). Appl. Organomet. Chem. 7, 357.

    Article  CAS  Google Scholar 

  20. Y. Hoshimoto, M. Ohashi, and S. Ogoshi (2011). J. Am. Chem. Soc. 133, 4668.

    Article  CAS  Google Scholar 

  21. S. Ogoshi, Y. Hoshimoto, and M. Ohashi (2010). Chem. Commun. 46, 3354.

    Article  CAS  Google Scholar 

  22. J. Li, J. C. Shi, H. F. Han, Z. Q. Guo, H. B. Tong, X. H. Wei, D. S. Liu, and M. F. Lappert (2013). Organometallics 32, 3721.

    Article  CAS  Google Scholar 

  23. D. Ulrich and H. Jankowski (1988). Chem. Tech. 40, 393.

    CAS  Google Scholar 

  24. W. C. Child and H. Adkins (1925). J. Am. Chem. Sco. 47, 798.

    Article  CAS  Google Scholar 

  25. T. Saegusa and T. Ueshima (1968). J. Org. Chem. 33, 3310.

    Article  CAS  Google Scholar 

  26. T. Seki, K. Akutsu, and H. Hattori (2001). Chem. Commun. 11, 1000.

    Article  Google Scholar 

  27. T. Seki and M. Onaka (2005). Chem. Lett. 34, 262.

    Article  CAS  Google Scholar 

  28. T. Seki and M. Onaka (2006). J. Phys. Chem. B. 110, 1240.

    Article  CAS  Google Scholar 

  29. Y. Hon, C. Chang, and Y. Wong (2004). Tetrahedron Lett. 45, 3313.

    Article  CAS  Google Scholar 

  30. J. A. Francis, S. G. Bott, and A. R. Barron (2000). J. Organomet. Chem. 597, 29.

    Article  CAS  Google Scholar 

  31. McMahon C.N., Francis J.A., Bott S.G., and Barron A. R. (1999). J. Chem. Soc., Dalton Trans. 67.

  32. J. A. Francis, S. G. Bott, and A. R. Barron (1999). Polyhedron 18, 2211.

    Article  CAS  Google Scholar 

  33. Francis J. A., Bott S. G., and Barron A. R. (1998). J. Chem. Soc. Dalton Trans. 3305.

  34. J. A. Francis, C. N. McMahon, S. G. Bott, and A. R. Barron (1999). Organometallics 18, 4399.

    Article  CAS  Google Scholar 

  35. M. L. Sierra, V. S. J. de Mel, and J. P. Oliver (1989). Organometallics 8, 2486.

    Article  CAS  Google Scholar 

  36. I. Yamaguchi, T. Iijima, and T. Yamamoto (2002). J. Organometal. Chem. 654, 229.

    Article  CAS  Google Scholar 

  37. Robson D. A., Rees L. H., Mountford P., and Schröder M. (2000). Chem. Commun. 1269.

  38. D. A. Robson, S. Y. Bylikin, M. Cantuel, N. A. H. Male, L. H. Rees, P. Mountford, and M. Schröder (2001). J. Chem. Soc., Dalton Trans. 2, 157.

    Article  Google Scholar 

  39. W. H. Sun, M. Shen, W. J. Zhang, W. Huang, S. F. Liu, and C. Redshaw (2011). Dalton Trans. 40, 2645.

    Article  CAS  Google Scholar 

  40. T. Ooi, K. Ohmatsu, K. Sasaki, T. Miura, and K. Maruoka (2003). Tetrahedron Lett. 44, 3191.

    Article  CAS  Google Scholar 

  41. B. Koning, J. Buter, R. Hulst, R. Stroetinga, and R. M. Kellogg (2000). Eur. J. Org. Chem. 15, 2735.

    Article  Google Scholar 

  42. G. M. Sheldrick SADABS Correction Software (University of Göttingen, Germany, 1996).

    Google Scholar 

  43. G. M. Sheldrick SHELX97, Program for Crystal Structure Refinement (University of Göttingen, Germany, 1997).

    Google Scholar 

  44. SHELXTL Program for Crystal Structure Refinement (Bruker Analytical X-ray Instruments Inc, Madison, 1998).

    Google Scholar 

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Acknowledgments

Financial support from the National Natural Science Foundation of China (Nos. 21272142, 51174275) and the Natural Science Foundation of Shanxi Province (Nos. 2011021011-1, 2008011021) are gratefully acknowledged.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engneering, Shanxi University, Taiyuan, 030006, People’s Republic of China

    Hong-Fei Han, Shao-Feng Zhang & Xue-Hong Wei

  2. Department of Chemistry, Taiyuan Normal University, Taiyuan, 030031, People’s Republic of China

    Hong-Fei Han

  3. Institute of Applied Chemistry, Shanxi University, Taiyuan, 030006, People’s Republic of China

    Zhi-Qiang Guo & Hong-Bo Tong

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  1. Hong-Fei Han
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  2. Shao-Feng Zhang
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Correspondence to Xue-Hong Wei.

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Han, HF., Zhang, SF., Guo, ZQ. et al. Synthesis, Crystal Structures and their Utilities in Tishchenko Reaction of N,O-Bidentate Aluminum Compounds. J Clust Sci 26, 1971–1982 (2015). https://doi.org/10.1007/s10876-015-0890-x

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  • DOI: https://doi.org/10.1007/s10876-015-0890-x

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