Structure and dynamic behavior of phosphine gold(I)-coordinated enamines: Characterization of α-metalated iminium ions

Organometallics

Volumn 33, Issue 16, 2014, Pages 4157-4164

  Sriram, Madhavi ^a   Zhu, Yuyang ^a   Camp, Andrew M ^a   Day, Cynthia S ^a   Jones, Amanda C ^a  

^a WAKE FOREST UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; GOLD; ISOMERS; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS COMPOUNDS; X RAY CRYSTALLOGRAPHY;

BINDING CONSTANT; C-C DOUBLE BONDS; COORDINATION MODES; GOLD COMPLEXES; INTRAMOLECULAR HYDROAMINATION; PHOSPHINE LIGANDS; STRUCTURE AND DYNAMICS; TRIETHYLAMINES;

GOLD COMPOUNDS;

EID: 84906568957     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om500670z     Document Type: Article

References (30)

1. Hesp, K. D.; Stradiotto, M. J. Am. Chem. Soc. 2010, 132, 18026-18029
2. Duan, H.; Sengupta, S.; Petersen, J. L.; Akhmedov, N. G.; Shi, X. J. Am. Chem. Soc. 2009, 131, 12100-12102
3. Enomoto, T.; Obika, S.; Yasui, Y.; Takemotoa, Y. Synlett 2008, 1647-1650
4. Lavallo, V.; Wright, J. H.; Tham, F. S.; Quinlivan, S. Angew. Chem., Int. Ed. 2013, 52, 3172-3176
5. Zeng, X.; Kinjo, R.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2010, 49, 942-945
6. Frey, G. D.; Kinjo, R.; Donnadieu, B.; Bertrand, G. J. Am. Chem. Soc. 2009, 131, 8690-8696
7. Zeng, X.; Frey, G. D.; Kousar, S.; Bertrand, G. Chem. Eur. J. 2009, 15, 3056-3060
8. Lavallo, V.; Frey, G. D.; Donnadieu, B.; Soleilhavoup, M.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 5224-5228
9. Young, P. C.; Green, S. L. J.; Rosair, G. M.; Lee, A.-L. Dalton Trans. 2013, 42, 9645-9653
10. Fürstner, A.; Alcarazo, M.; Goddard, R.; Lehmann, C. W. Angew. Chem., Int. Ed. 2008, 47, 3210-3214
11. Liu, X.-Y.; Guo, Z.; Dong, S. S.; Li, X.-H.; Che, C.-M. Chem. Eur. J. 2011, 17, 12932-12945
12. Han, Z.-Y.; Ziao, H.; Chen, Z.-H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 9182-9183
13. We have made many observations similar to those in the work reported here: Zhdanko, A.; Maier, M. E. Angew. Chem., Int. Ed. 2014, 53, 7760-7764
14. Brooner, R. E. M.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2013, 52, 11714-11724 and references therein
15. Zhu, Y.; Day, C. S.; Jones, A. C. Organometallics 2012, 31, 7332-7335
16. Hooper, T. N.; Green, M.; McGrady, J. E.; Patel, J. R.; Russell, C. A. Chem. Commun. 2009, 3877-3879
17. White, W. A.; Weingarten, H. J. Org. Chem. 1967, 32, 213-214
18. Simonneau, A.; Garcia, P.; Goddard, J.-P.; Mouriès-Mansuy; Malacria, M.; Fensterbank, L. Beilstein J. Org. Chem. 2011, 7, 1379-1386
19. Barluenga, J.; Diéguez, A.; Fernández, A.; Rodríguez, F.; Fañanás, F. J. Angew. Chem., Int. Ed. 2006, 45, 2091-2093
20. Guan, H.; Iimura, M.; Magee, M. P.; Norton, J. R.; Zhu, G. J. Am. Chem. Soc. 2005, 127, 7805-7814
21. These values are very close to values predicted by recent computational studies: Ciancaleoni, G.; Rampino, S.; Zuccaccia, D.; Tarantelli, F.; Belanzoni, P.; Belpassi, L. J. Chem. Theory Comput. 2014, 10, 1021-1034
22. In a Pt(IV) enamine, the Pt-C-C angle is 96.4 °C; the authors assign this to be intermediate between π-complex characterization and iminium alkyl: Béthegnies, A.; Daran, J.-C.; Poli, R. Organometallics 2013, 32, 673-681
23. Brown, K. L.; Damm, L.; Dunitz, J. D.; Eschenmoser, A.; Hobi, R.; Kratky, C. Helv. Chim. Acta 1978, 61, 3108-3135
24. Reich, H. J. J. Chem. Educ. 1995, 72, 1086
25. Roberts, J. D.; Hawkins, B. L.; Bremser, W.; Borcic, S. J. Am. Chem. Soc. 1971, 93, 4472-4479
26. Brown, T. J.; Dickens, M. G.; Widenhoefer, R. A. Chem. Commun. 2009, 6451-6453
27. Zhdanko, A.; Ströbele, M.; Maier, M. E. Chem. Eur. J. 2012, 18, 14732-14744
28. Brooner, R. E. M.; Brown, T. J.; Widenhoefer, R. A. Chem. Eur. J. 2013, 19, 8276-8284
29. Shapiro, N. D.; Toste, F. D. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 2779-2782
30. Although such structures do not represent alkyne amination products, they are key intermediates in gold-catalyzed processes, and gold-mediated isomerization has been proposed: Montserrat, S.; Faustino, H.; Lledós, A.; Mascareñas, J. L.; López, F.; Ujaque, G. Chem. Eur. J. 2013, 19, 15248-15260