A phosphine gold(i) π-alkyne complex: Tuning the metal alkyne bond character and counterion position by the choice of the ancillary ligand

Inorganic Chemistry

Volumn 49, Issue 7, 2010, Pages 3080-3082

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

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77950240546     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic100093n     Document Type: Article

References (44)

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.
3. Hashrni. A. S. K. Chem. Rev. 2007, 107, 3180-3211.
4. Li, Z.; Brouwer. C.; He, C. Chem. Rev. 2008, 108, 3239-3265.
5. Jiménez-Nnez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326-3350.
6. Li, H.; Widenhoefer, R. A. Org. Lett. 2009, 11, 2671-2674.
7. Zeng, X.; Soleffliavoup, M.; Bertrand, G. Org. Lett. 2009, 11, 3166-3169.
8. Zeng, X.; Frey, G. D.; Kinjo, R.; Donnadicu, B.; Bertrand, G. J. Am. Chem. Soc. 2009, 131, 8690-8696.
9. Schmidbaur, H.; Schier, A. Organometallics 2010, 29, 2-23.
10. Arcadi, A. Chem. Rev. 2008, 108, 3266.
11. Bongers, N.; Krause, N. Angew. Chem., Int. Ed. 2008, 47, 2178.
12. A limited number of gold(I)-coordinated metal alkynyls and spectroscopieally detected gold alkynes are known: (a) Lavallo, V.; Frey, G. D.; Kousar, S.; Donnadieu, B.; Bertrand, G. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 13569-13573.
13. (b) Akana, J. A.; Bhattacharyya, K. X.; Mueller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2007, 129, 7736-7737.
14. (c) Lavallo, V.; Frey, G. D.; Donnadieu, B.; Soleilhavoup, M.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 5224-5228.
15. (d) Wu, J.; Kroll, P.; Dias, H. V. R. Inorg. Chem. 2009, 48, 423-425.
16. (e) Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415-1417.
17. (f) Flagge, S.; Anoop, A.; Goddard, R.; Thiel, W.; Furstner, A. Chem.Eur. J. 2009, 15, 8558-8565.
18. (g) Dias, R. H. V.; Flores, J. A.; Wu, J. A J.; Kroll, P. J. Am. Chem. Soc. 2009, 131, 11249-11255.
19. (a) To the best of our knowledge, only bimetallic encumbered alkynetethered phosphinegold(I) complexes have been synthesized: Shapiro, N. D.; Toste, F. D. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 2779-2782.
20. 6 complexes: Hopper, T. N.; Green, M.; Russell, C. A. Chem. Commun. 2010, DOI:10.1039/b923900f.
21. Macchioni, A. Chem. Rev. 2005, 105, 2039-2073.
22. Brouwer, C.; He, C. Angew. Chem., Int. Ed. 2006, 45, 1744-1747.
23. Schelwies, M.; Dempwolff, A. L.; Rominger, F.; Heimchen, G. Angew. Chem., Int. Ed. 2007, 46, 5598-5601.
24. Zhang, Z.; Widenhoefer, R. A. Org. Lett. 2008, 10, 2079-2081.
25. Tarseili, M. A.; Chianese, A. R.; Lee. S. J.; Gagnè, M. R. Angew. Chem., Int. Ed. 2007, 46, 6670-6673.
26. Xia, Y.; Dudnik, A. S.; Gevorgyan, V.; Li, Y. J. Am. Chem. Soc. 2008, 130, 6940-6941.
27. Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496-499.
28. LaLonde, R. L.; Sherry, B. D.; Kang, E. J.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2452-2453.
29. For a recent review on the theoretical chemistry of gold, see: Pyykkö, P. Chem. Soc. Rev. 2008, 37, 1967-1997.
30. The stability of analogous complexes with terminal alkynes is much reduced.
31. Belpassi, L.; Infante, I.; Tarantelli, F.; Visscher, L. J. Am. Chem. Soc. 2008, 130, 1048-1060.
32. Macchioni, A. Eur. J. Inorg. Chem. 2003, 195-205 and references cited therein.
33. Zuccaccia, C.; Bellachioma, G.; Cardad, G.; Macchioni, A. J. Am. Chem. Soc. 2001, 123, 11020-11028.
34. Macchioni, A.; Magistrato, A.; Orabona, I.; Ruffo, F.; Rothlisberger, U.; Zuccaccia, C. New J. Chem. 2003, 27, 455-458.
35. -6 average): Neuhaus, D.; Williamson, M. The Nuclear Overhauser Effect in Structural and Conformational Analysis; VCH Publishers: New York, 1989.
36. Zuccaccia, D.; Belpassi, L.; Tarantelli, F.; Macchioni, A. J. Am. Chem. Soc. 2009, 131, 3170-3171.
37. Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
38. For a detailed study on olefin exchange in NHC and phosphinegold alkene complexes, see: (a) Brown, T. J.; Dickens, M. G.; Widenhoefer, R. A. J. Am. Chem. Soc. 2009, 131, 6350-6351.
39. (b) Brown, T. J.; Dickens, M. G.; Widenhoefer, R. A. Chem. Commun. 2009, 6451-6453.
40. (c) Hooper, T. N.; Green, M.; MeGrady, J. E.; Patela, J. R.; Russell, C. A. Chem. Commun. 2009, 3877-3879.
41. Note that, if the exchange mechanisms were dissociative, different rates would likely imply different interaction energies, in contrast with our calculations.
42. 4.
43. 3: Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed, 2002, 41, 4563-4565.
44. NHC: Marion, N.; Ramòn, R. S.; Nolan, S. P. J. Am. Chem. Soc. 2009, 131, 448-449.