The synthesis, characterization, and catalytic properties of (2-C,N) palladacycles with N-heterocyclic carbene-based ancillary ligands
The synthesis, characterization, and catalytic properties of (2-C,N) palladacycles with N-heterocyclic carbene-based ancillary ligands
Novel ve-membered (K2-C,N)-palladacyclic complexes were prepared from the reaction of the corresponding acetate-bridged palladacycle dimer with N-heterocyclic carbene (NHC) ligands in high yields. Palladacyclic complexes ( 3 ) were fully characterized by elemental analysis and 1 H and 13 C NMR spectroscopy. Palladacyclic complexes were tested as catalyst for the C{C bond forming reaction. These complexes were found to be efficient catalysts for the Suzuki{Miyaura reaction of aryl bromides.
___
- 1. Selander, N.; Szabo, K. J. Chem. Rev . 2011 , 111 , 2048{2076.
- 2. Dupont, J.; Pfeffer, M. Palladacycles ; Wiley-VCH: Weinheim, Germany, 2008.
- 3. Ratti, R. Can. Chem. Trans . 2014 , 2 , 467{488.
- 4. Tsuji, J. Palladium Reagents and Catalysts ; Wiley: Chichester, UK, 2004.
- 5. Bedford, R. B.; Cazin, C. S. J.; Holder, D. Coord. Chem. Rev . 2004 , 248 , 2283{2321.
- 6. Dupont, J.; Consorti, C. S.; Spencer. J. Chem. Rev. 2005 , 105 , 2527{2571.
- 7. Lu, Z.; Wang, X.; Liu, B.; Wang, R. J. Organomet. Chem. 2010 , 695 , 2191{2200.
- 8. Alacid, E.; Alonso, D. A.; Botella, L.; Najera, C.; Pacheco. M. C. Chem. Rec . 2006 , 6 , 117{132.
- 9. Herrmann, W. A.; Ofele, K.; Preysing, D.; Schneider, S. K. J. Organomet. Chem . 2003 , 687 , 229{248.
- 10. Gunay, M. E.; Gumusada, R.; Ozdemir, N.; Dincer, M.; Cetinkaya, B. J. Organomet. Chem . 2009 , 694 , 2343{2349.
- 11. Miyaura, N.; Suzuki, A. Chem. Rev . 1995 , 95 , 2457{2483.
- 12. Peris,E.; Crabtree, R. H. Coord. Chem. Rev . 2004 , 248 , 2239{2246.
- 13. Budagumpi, S.; Haque, R. A.; Salman, A. W. Coord. Chem Rev . 2012 , 256 , 1787{1830.
- 14. Wang, D.; Astruc, D. Chem. Rev . 2015 , 115 , 6621{6686.
- 15. Hamad, F. B.; Sun, T.; Xiao, S.; Verpoort, F. Coord. Chem. Rev . 2013 , 257 , 2274{2292.
- 16. Taige, M. A.; Ahrens, S.; Strassner, T. J. Organomet. Chem . 2011 , 696 , 2918{2927.
- 17. Li, J.; Yu, A.; Wu, Y.; Zhu, Y.; Du, C.; Yang, H. Polyhedron 2007 , 26 , 2629{2637.
- 18. Yu, H. W.; Shi, J. C.; Zhang, H.; Yang, P. Y.; Wang, X. P.; Jin Z. L. J. Mol. Catal. A : Chem . 2006 , 250 , 15{19.
- 19. Linninger, C. S.; Herdtweck, E.; Hoffmann, S. D.; Herrmann, W. A.; Kuhn, F. E. J. Mol. Struct. 2008 , 890 , 192{197.
- 20. Arentsen, K.; Caddick, S.; Cloke, F. G. N.; Herring, A. P.; Hitchcock, P. B. Tetrahedron Lett . 2004 , 45 , 3511{3515.
- 21. Beller, M.; Fischer, H.; Herrmann, W. A.; Ofele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl . 1995 , 34 , 1848{ 1849.
- 22. Viciu, M. S.; Grasa, G. A.; Nolan, S. P. Organometallics 2001 , 20 , 3607{3612.
- 23. Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem . 2004 , 69 , 3173{3180.
- 24. Wu, K. M.; Huang, C. A.; Peng, K. F.; Chen, C. T. Tetrahedron 2005 , 61 , 9679{9687.
- 25. Palencia, H.; Garcia-Jimenez, F.; Takacs, J. M. Tetrahedron Lett . 2004 , 45 , 3849{3853.
- 26. Aiello, I.; Crispini, A.; Ghedini, M.; La Deda, M.; Barigelletti, F. Inorg. Chim. Acta 2000 , 308 , 121{128.
- 27. Zeng, X.; Yang, X.; Zhang, Y.; Qing, C.; Zhang, H. Bioorg . Med . Chem . Lett . 2010 , 20 , 1844{1847.
- 28. van der Made, A. W.; van der Made, R. H. J. Org. Chem . 1993 , 58 , 1262{1263.