An efficient ligand-free method for the transfer hydrogenation of ketones and aldehydes catalyzed by different complexes
A very efficient ligand-free method was developed for the transfer hydrogenation of ketones and aldehydes catalyzed by different metal complexes. With this catalytic system, the catalytic performance and catalytic stability of different Ir, Ru, and Pd complexes were more favorable than those of the previously reported systems for transfer hydrogenation. This ligand-free catalytic system showed good stability and excellent activity even with lower catalyst concentrations for the ketones and aldehydes tested.
An efficient ligand-free method for the transfer hydrogenation of ketones and aldehydes catalyzed by different complexes
A very efficient ligand-free method was developed for the transfer hydrogenation of ketones and aldehydes catalyzed by different metal complexes. With this catalytic system, the catalytic performance and catalytic stability of different Ir, Ru, and Pd complexes were more favorable than those of the previously reported systems for transfer hydrogenation. This ligand-free catalytic system showed good stability and excellent activity even with lower catalyst concentrations for the ketones and aldehydes tested.
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- Albrecht, M. J.; Miecznikowski, R.; Samuel, A.; Faller, J. W.; Crabtree, R. H. Organometallics 2002, 21, 3596–3604. Zinner, S. C.; Rentzsch, C. F.; Herdtweck, E.; Herrmann, W. A.; K¨ uhn, F. E. Dalton Trans. 2009, 35, 7055–7062. (a) T¨ urkmen, H.; Pape, T.; Hahn, F. E.; C ¸ etinkaya, B. Organometallics 2008, 27, 571–575: (b) T¨ urkmen, H.; Pape, T.; Hahn, F. E.; C ¸ etinkaya, B. Eur. J. Inorg. Chem. 2008, 36, 5418–5423.
- Marza, E.; Sanau, M.; Peris, E. Inorg. Chem. 2005, 44, 9961–9967.
- Sun, J.-F.; Chen, F. B.; Dougan, A.; Xu, H.-J.; Cheng, Y.; Li, Y.-Z.; Chen, X.-T.; Xue, Z.-L. J. Organomet. Chem. 2009, 694, 2096–2105.
- (a) Binobaid, A.; Iglesias, M.; Beetstra, D.; Dervisi, A.; Fallis, I.; Cavell, K. J. J. Eur. Inorg. Chem. 2010, 34, 5426–5431; (b) G¨ urb¨ uz, N.; Ya¸sar, S.; ¨ Ozcan, E. ¨ O.; ¨ Ozdemir, I.; C ¸ etinkaya, B. Eur. J. Inorg. Chem. 2010, 19, 3051–3056; (c) ¨ Ozdemir, I.; Ya¸sar, S.; C ¸ etinkaya, B. Trans. Metal Chem. 2005, 30, 831–835.
- Aupoix, A.; Bournaud, C.; Thanh, G. V. Eur. J. Org. Chem. 2011, 2772–2776.
- Enthaler, S.; Jackstell, R.; Hagemann, B.; Junge, K.; Erre, G.; Beller, M. J. Org. Chem., 2006, 691, 4652–4659. Ya¸sar, S.; Cavell, K. J.; Ward, B. D.; Kariuki, B. App. Organomet. Chem. 2011, 25, 374–382.
- Gulcemal, S.; Daran, J. C.; Cetinkaya, B. Inorganica Chimica Acta 2011, 365, 264–268.
- Kitamura, M.; Noyori R. In Rutenium in Organic Synthesis; Murashashi, S. I., Ed.; Wiley-VCH, Weinheim, 2004, pp. 3–43
- Baude, E. A.; Linstead, R. P. J. Chem. Soc. 1954, 3544–3547.
- (a) Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226–236; (b) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 51, 1051–1069.
- (a) Albrecht, M.; Miecznikowski, J. R.; Samuel, A.; Faller, J. W.; Crabtree, R. H. Organometallics 2002, 21, 3596–3604; (b) Herrmann, W. A.; Baskakov, D. E.; Hoffmann, S. D.; Bunlaksananusorn, T.; Rampf, F.; Rodefeld, L. Organometallics 2006, 25, 2449–2456.
- Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97–102; ((b) B¨ ackvall, J.-E. J. Organomet. Chem. 2002, 652, 105–111.
- Guijarro, D.; Oscar, P.; Yus, M. Tetrahedron Lett. 2011, 52, 789–791.
- Yong, G.; Zhang, Y.; Ying, Y. Angew. Chem., Int. Ed. 2008, 47, 9345–9348.
- Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226–236.
- Exner, C.; Pfaltz, A.; Studer, M.; Blaser, H. Adv. Synth. Catal. 2003, 345, 1253–1260.
- Zhu, Y.; Qian, H.; Drake, B. A.; Jin, R. Angew. Chem., Int. Ed. 2010, 49, 1295–1298.
- (a) Gnanamgari, D.; Sauer, E. L. O.; Schley, N. D.; Butler, C.; Incarvito, C. D.; Crabtree, R. H. Organometallics 2009, 28, 321–325; (b) Wylie, W. N. O.; Lough, A. J.; Morris, R. H. Organometallics 2012, 31, 2152–2165.
- Aupoix, A.; Bournaud, C.; Vo-Thanh, G. Eur. J. Org. Chem. 2011, 15, 2772–2776.
- (a) Enthaler, S.; Jackstell, R.; Hagemann, B.; Junge, K.; Erre, G.; Beller, M. J. Organomet. Chem. 2006, 691, 4652–4659; (b) Ya¸sar, S.; Cavell, K. J.; Ward, B. D.; Kariuki, B. App. Organomet. Chem. 2011, 25, 374–382.
- Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97–102.
- Hillier, A. C.; Lee, H. M.; Stevens, E. D.; Nolan, S. P. Organometallics 2001, 20, 4246–4252.
- Sakaguchi, S.; Yamaga, T.; Ishii, Y. J. J. Org. Chem. 2001, 6 6, 4710–4712.
- Ikhile, M. I.; Nyamori, V. O.; Bala, M. D. Tetrahedron Lett. 2012, 53, 4925–4928.
- Sedelmeier, J.; Ley, S. V.; Baxendale, I. R. Green Chem. 2009, 11, 683–685.
- Polshettiwar, V.; Varma, R. S. Green Chem. 2009, 11, 1313–1316.
- G¨ urb¨ uz, N.; ¨ Ozcan, E. ¨ O.; ¨ Ozdemir, I.; C ¸ etinkaya, B.; S ¸ahin, O.; B¨ uy¨ ukg¨ ung¨ or, O. Dalton Trans. 2012, 41, 2330–2339.