Ion pairing in cationic olefin-gold(I) complexes

Journal of the American Chemical Society

Volumn 131, Issue 9, 2009, Pages 3170-3171

  Zuccaccia, Daniele ^a   Belpassi, Leonardo ^a   Tarantelli, Francesco ^a   Macchioni, Alceo ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; DENSITY FUNCTIONAL THEORY; DYES; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; POSITIVE IONS; STYRENE;

ANCILLARY LIGANDS; COUNTERIONS; DENSITY FUNCTIONAL THEORY CALCULATIONS; IMIDAZOL-2-YLIDENE; ION PAIRING; NHC LIGANDS; NMR SPECTROSCOPY; POSITIVE CHARGES; RELATIVE ANIONS; RELATIVISTIC EFFECTS;

GOLD COMPOUNDS;

ALKENE; GOLD COMPLEX; GOLD; ION; ORGANOGOLD COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; LOW TEMPERATURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODEL; CHEMISTRY; COMPUTER SIMULATION;

ALKENES; COMPUTER SIMULATION; GOLD; IONS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; ORGANOGOLD COMPOUNDS;

EID: 67749139799     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja809998y     Document Type: Article

References (34)

1. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351-3378.
2. Marion, N.; Nolan, S. P. Chem. Soc. Rev. 2008, 37, 1776-1782, and references therein.
3. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211, and references therein.
4. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239-3265, and references therein.
5. Jiménez-Nùnez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326-3350, and references therein.
6. Brouwer, C.; He, C. Angew. Chem., Int. Ed. 2006, 45, 1744-1747.
7. Schelwies, M.; Dempwolff, A. L.; Rominger, F.; Helmchen, G. Angew. Chem., Int. Ed. 2007, 46, 5598-5601.
8. Zhang, Z.; Widenhoefer, R. A. Org. Lett. 2008, 10, 2079-2081.
9. Tarselli, M. A.; Chianese, A. R.; Lee, S. J.; Gagnè, M. R. Angew. Chem., Int. Ed. 2007, 46, 6670-6673.
10. Xia, Y.; Dudnik, A. S.; Gevorgyan, V.; Li, Y. J. Am. Chem. Soc. 2008, 130, 6940-6941.
11. Hamilton, G. L.; Kang, E. J.; Mba, M.; F. Dean Toste, F. D. Science 2007, 317, 496-499.
12. LaLonde, R. L.; Sherry, B. D.; Kang, E. J.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2452-2453.
13. Macchioni, A. Chem. Rev. 2005, 105, 2039-2073, and references therein.
14. Kovàcs, G.; Ujaque, G.; Lledòs, A. J. Am. Chem. Soc. 2008, 130, 853-864.
15. Gourlaouen, C.; Marion, N.; Nolan, S. P.; Maseras, F. Org. Lett. 2009, 11, 81-84.
16. For a recent review on the theoretical chemistry of gold, see: Pyykkö, P. Chem. Soc. Rev. 2008, 37, 1967-1997.
17. +, see: Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798-1799.
18. +, see: de Frémont, P.; Stevens, E. D.; Fructos, M. R.; Dýaz-Requejo, M. M.; Perez, P. J.; Nolan, S. P. Chem. Commun. 2006, 2045-2047.
19. Corberan, R.; Ramýrez, J.; Poyatos, M.; Peris, E.; Fernandez, E. Tetrahedron: Asymmetry 2006, 17, 1759-1762.
20. For partial characterization of olefin Au (I) complexes with PPh3, see: Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415-1417.
21. Garcìa-Mota, M.; Cabello, N.; Maseras, F.; Antonio, M.; Echavarren, A. M.; Pèrez-Ramìrez, J.; Lopez, N. Chem. Phys. Chem. 2008, 9, 1624-1629.
22. Grisé, C. M.; Rodrigue, E. M.; Barriault, L. Tetrahedron 2008, 64
23. A styrene Au (I) complex supported by the 2, 2′-bipyridine ligand has been characterized through X-ray single crystal studies: Cinellu, M. A.; Minghetti, G.; Cocco, F.; Stoccoro, S.; Zucca, A.; Manassero, M.; Arca, M. Dalton Trans. 2006, 5703-5716.
24. For olefin Au (I) complexes with more hindered phosphines, see: Herrero-Gómez, E.; Nieto-Oberhuber, C.; López, S.; Benet-Buchholz, J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 5455-5459.
25. For olefin-tethered posphine Au (I) complexes, see: Shapiro, N. D.; Toste, F. D. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 2779-2782.
26. For arene Au (I) complexes with NHC see: Lavallo, V.; Frey, G. D.; Kousar, S.; Donnadieu, B.; Bertrand, G. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 13569-13573.
27. For alkyne Au (I) complexes with NHC, see: Akana, A. J.; Bhattacharyya, K. X.; Peter Muller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2007, 129, 7736-7737.
28. Au (I) systems where the charge on gold was estimated to be less than the nominal unity have been reported. For example, see: Pyykkö, P.; Schneider, W.; Bauer, A.; Bayler, A.; Schmidbaur, H. Chem. Commun. 1997, 1111-1112.
29. Macchioni, A. Eur. J. Inorg. Chem. 2003, 19, 5-205, and references therein.
30. Macchioni, A.; Ciancaleoni, G.; Zuccaccia, C.; Zuccaccia, D. Chem. Soc. Rev. 2008, 37, 479-489, and references therein.
31. A similar location of the counterion has been previously found in NHC Ir (III) complexes: Appelhans, L. N.; Zuccaccia, D.; Kovacevic, A.; Chianese, A. R.; Miecznikowski, J. R.; Macchioni, A.; Clot, E.; Eisenstein, O.; Crabtree, R. H. J. Am. Chem. Soc. 2005, 127, 16299-16311.
32. A spatial confinement of the counterion due to a perpendicular disposal of aryl moieties with hindered ortho-substituents has been observed in squareplanar olefin Pd (II) and Pt (II) complexes bearing α-diimine ligands: Zuccaccia, C.; Macchioni, A.; Orabona, I.; Ruffo, F. Organometallics 1999, 18, 4367-4372.
33. Macchioni, A.; Magistrato, A.; Orabona, I.; Ruffo, F.; Rothlisberger, U.; Zuccaccia, C. New J. Chem. 2003, 27, 455-458.
34. Binotti, B.; Bellachioma, G.; Cardaci, G.; Carfagna, C.; Zuccaccia, C.; Macchioni, A. Chem.-Eur. J. 2007, 13, 1570-1582.