(N-heterocyclic carbene)PdCl2(TEA) complexes: Studies on the effect of the "throw-away" ligand in catalytic activity

Organometallics

Volumn 30, Issue 18, 2011, Pages 5052-5056

  Chen, Ming Tsz ^a   Vicic, David A ^a   Turner, Michael L ^b   Navarro, Oscar ^a  

^a UNIVERSITY OF HAWAII   (United States)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

N-HETEROCYCLIC CARBENES; SUZUKI-MIYAURA; TRIETHYLAMINES;

CARBON INORGANIC COMPOUNDS; CATALYST ACTIVITY; LIGANDS; PALLADIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

EID: 80052990360     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200699p     Document Type: Article

References (33)

1. Tsuji, J. Palladium Reagents and Catalysis, 2 nd ed.; Wiley: West Sussex, England, 2004.
2. de Meijere, A., Diederich, F., Ed. Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; Wiley-VCH: Weinheim, Germany, 2004.
3. Negishi, E., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002.
4. Navarro, O.; Nolan, S. P. C-C Bond Formation by Cross-Coupling. In Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, M. P., Eds.; Elsevier: New York, 2007; Vol. 11, Chapter 1.
5. Miyaura, N.; Yamada, K.; Suzuki, A. Tetrrahedron Lett. 1979, 36, 3437-3439
6. Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301-302
7. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636-3638
8. Stephen, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313-3315
9. Dieck, H. A.; Heck, R. F. J. Organomet. Chem. 1975, 93, 259-263
10. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedrom Lett. 1975, 4467-4470
11. Chodkiewicz, W.; Cadiot, P. Compt. Rend. Hebd. Seances Acad. Sci. 1955, 214, 1055-1057
12. Negishi, E. Aspects Mech. Organomet. Chem. 1978, 285-317
13. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387-3388
14. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723
15. Oh-e, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201-2208
16. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028
17. Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866-2873
18. Brenstrum, T.; Gerristma, D. A.; Adjabeng, G. M.; Frampton, C. S.; Britten, J.; Robertson, A. J.; McNulty, J.; Capretta, A. J. Org. Chem. 2004, 69, 7635-7639
19. Takagi, J.; Takahashi, T. I.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 8001-8006
20. Viciu, M. S.; Germeneau, R. F.; Navarro-Fernandez, O.; Stevens, E. D.; Nolan, S. P. Organometallics 2002, 21, 5470-5472
21. For an illustrative example, see: Lebel, H.; Janes, M. K.; Charette, A. B.; Nolan, S. P. J. Am. Chem. Soc. 2004, 126, 5046-5047
22. Organ, M. G.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J; Valente, C. Chem. Eur. J. 2006, 12, 4749-4755
23. Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101-4111
24. Viciu, M. S.; Navarro, O.; Germaneau, R. F.; Kelly, R. A., III; Sommer, W.; Marion, N.; Stevens, E. D.; Cavallo, L.; Nolan, S. P. Organometallics 2004, 23, 1629-1635
25. Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274-7276
26. Fors, B. P.; Watson, D. A.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 13552-13554
27. Chass, G. A.; O'Brien, C. J.; Hadei, N.; Kantchev, E. A. B.; Mu, W.-H.; Fang, D.-C.; Hopkinson, A. C.; Csizmadia, I. G.; Organ, M. G. Chem. Eur. J. 2009, 15, 4281-4288
28. Valente, C.; Belovich, M. E.; Hadei, N.; Organ, M. G. Eur. J. Org. Chem. 2010, 4343-4354
29. Organ, M. G.; Chass, G. A.; Fang, D.-C.; Hopkinson, A. C.; Valente, C. Synthesis 2008, 2776-2797
30. Nasielski, J.; Hadei, N.; Achonduh, G.; Kantchev, E. A. B.; O'Brien, C. J.; Lough, A.; Organ, M. G. Chem. Eur. J. 2010, 16, 10844-10853
31. Valente, C.; Baglione, S.; Candito, D.; O'Brien, C. J.; Organ, M. G. Chem. Commun. 2008, 735-737
32. Hadei, N.; Valente, C.; O'Brien, C. J.; Organ, M. G. Angew. Chem., Int. Ed. 2011, 50, 3896-3899
33. Diebolt, O.; Jurčik, V.; Correa da Costa, R.; Braunstein, P.; Cavallo, L.; Nolan, S. P.; Slawin, A. M. Z.; Cazin, C. S. J. Organometallics 2010, 29, 1443-1450