Synthesis of well-defined N-heterocyclic carbene silver(I) complexes

Organometallics

Volumn 24, Issue 26, 2005, Pages 6301-6309

  De Frémont, Pierre ^a   Scott, Natalie M ^a   Stevens, Edwin D ^a   Ramnial, Taramatee ^b   Lightbody, Owen C ^b   Macdonald, Charles L B ^c   Clyburne, Jason A C ^b   Abernethy, Colin D ^d   Nolan, Steven P ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

^b SIMON FRASER UNIVERSITY   (Canada)

^c UNIVERSITY OF WINDSOR   (Canada)

^d KEENE STATE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIRECT METALATION; IMIDAZOLIUM CHLORIDE SALTS; N-HETEROCYCLIC CARBENE (NHC);

CHLORIDE MINERALS; COMPLEXATION; HALIDE MINERALS; ORGANIC SOLVENTS; SALTS; SILVER COMPOUNDS;

ORGANOMETALLICS;

EID: 30344459392     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050735i     Document Type: Article

References (50)

1. Ölefe, K. J. Organomet. Chem. 1968, 12, 42-43.
2. Wanzlick, H.-W.; Schönherr, H.-J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141-142.
3. Arduengo, A. J. III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
4. (a) Heinemann, W. A.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023-2038.
5. (b) Hermann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187.
6. (c) Gründemann, S.; Albrecht, M.; Loch, J. A.; Faller, J. W.; Crabtree, R. H. Organometallics 2001, 20, 5485-5488.
7. (d) McGuiness, D. S.; Cavell, K. J.; Skelton, B. W.; White, A. H. Organometallics 1999, 18, 1596-1605.
8. (e) Simms, R. W.; Drewitt, M. J.; Baird, M. C. Organometallics 2002, 21, 2958-2963.
9. (a) McGuinness, D. S.; Cavell, K. J. Organometallics 2000, 19, 741-748.
10. (b) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079-2082.
11. (c) Poyato, M.; Márquez, F.; Peris, E.; Claver, C.; Fernández, E. New J. Chem. 2003, 27, 425-431.
12. (d) Hermann, W. A.; Ölefe, K.; Von Preysing, D.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229-248.
13. (e) Lee, H. M.; Lu, C. Y.; Chen, C. Y.; Chen, W. L.; Lin, H. C.; Chiu, P. L.; Cheng, P. Y. Tetrahedron 2004, 60, 5807-5825.
14. (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
15. (b) Hillier, A.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69-82.
16. (c) Viciu, M. S.; Germaneau, R. F.; Navarro-Fernández, O.; Stevens, E. D.; Nolan, S. P. Organometallics 2002, 21, 5470-5472.
17. (a) Huang, J.; Stevens, E. D.; Nolan, S. P. Organometallics 2000, 19, 1194-1197.
18. (b) Delaude, L.; Szypa, M.; Demonceau, A.; Noels, A. F. Adv. Synth. Cat. 2002, 344, 749-756.
19. (c) Courchay, F.; Sworen, J. C.; Wagener, K. B. Macromolecules 2003, 36, 8231-8239.
20. (d) Choi, T.-L.; Grubbs, R. H. Angew. Chem., Int. Ed. 2003, 42, 1743-1746.
21. (e) Yao, Q.; Rodriguez Motta, A. Tetrahedron Lett. 2004, 45, 2447-2451.
22. (e) Gallivan, J. P.; Jordan, J. P.; Grubbs, R. H. Tetrahedron Lett. 2005, 46, 2577-2580.
23. (a) Albretch, M.; Miecznikowski, J. R.; Crabtree, R. H. Polyhedron 2004, 23, 2857-2872.
24. (b) Sprengers, J. W.; Wassenaar, J.; Clément, N. D.; Cavell, K. J.; Elsevier, C. J. Angew. Chem., Int. Ed. 2005, 44, 2026-2029.
25. (c) Dharmasena, U. L.; Foucault, H. M.; Dos Santos, E. N.; Fogg, D. E.; Nolan, S. P. Organometallics 2005, 24, 1056-1058.
26. (a) Larsen, A. O.; Leu, W.; Oberhuber, C. N.; Campbell, J. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 11130-11131.
27. (b) Kaur, H.; Kauer Zinn, F.; Stevens, E. D.; Nolan, S. P. Organometallics 2004, 23, 1157-1160.
28. (c) Díez-González, S.; Kaur, H.; Kauer Zinn, F.; Stevens, E. D.; Nolan, S. P. J. Org. Chem. 2005, 70, 4787-4796.
29. (a) Schneider, S. K.; Hermann, W. A.; Herdtwerck, E. Z. Anorg. Allg. Chem. 2003, 629, 2363-2370.
30. (b) Nieto Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402-2406.
31. Sentman, A. C.; Szilárd, C.; Waymouth, R. M.; Hedrick, J. L. J. Org. Chem. 2005, 70, 2391-2393.
32. Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972-975.
33. Lin, I. J. B.; Vasam, C. S. Comm. Inorg. Chem. 2004, 25, 75-129.
34. Arduengo, A. J. III.; Dias, H. V. R.; Calabrese, J. C.; Davidson, F. Organometallics 1993, 12, 3405-3409.
35. Baker, M. V.; Brown, D. H.; Haque, R. A.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 2004, 3756-3764.
36. Garrison, J. C.; Simons, R. S.; Talley, J. M.; Wesdemiotis, C.; Tessier, C. A.; Youngs, W. J. Organometallics 2001, 20, 1276-1278.
37. Kascatan-Nebioglu, A.; Panzer, M. J.; Garrison, J. C.; Tessier, C. A.; Youngs, W. J. Organometallics 2004, 23, 1928-1931.
38. Catalano, V. J.; Malwitz, M. A. Inorg. Chem. 2003, 5483-5485.
39. Liu, Q. X.; Xu, F.-B.; Li, Q. S.; Zeng, X.-S.; Leng, X.-B.; Chou, Y. L.; Zhang, Z.-Z. Organometallics 2003, 22, 309-314.
40. Chen, W.; Biao, W.; Matsumoto, K. J. Organomet. Chem. 2002, 654, 233-236.
41. Melaiye, A.; Simons, R. S.; Milsted, A.; Pingitore, F.; Wesdemiotis, C.; Tessier, C. A.; Youngs, W. J. J. Med. Chem. 2004, 47, 973-977.
42. Ramnial, T.; Abernethy, C. D.; Spicer, M. D.; McKenzie, I. D.; Gay, I. D.; Clyburne, J. A. C. Inorg. Chem. 2003, 42, 1391-1393.
43. De Frémont, P.; Scott, N. M.; Stevens, E. D.; Nolan, S. P. Organometallics 2005, 24, 2411-2418.
44. Herrmann, W. A.; Schneider, S. K.; Öfele, K.; Sakamoto, M.; Herdtweck, E. J. Organomet. Chem. 2004, 689, 2441-2449.
45. Lee, K. M.; Wang, H. M. J.; Lin, I. J. B. J. Chem. Soc., Dalton Trans. 2002, 14, 2852-2856.
46. Bildstein, B.; Malaun, M.; Kopacka, H.; Wurst, K.; Mitterböck, M.; Ongania, K.-H.; Opromolla, G.; Zanello, P. Organometallics 1999, 18, 4325-4386.
47. Clarke, A. J.; Ingleson, M. J.; Kociok-Köhn, G.; Mahon, M. F.; Patmore, N. J.; Rourke, J. P.; Ruggiero, G. D.; Weller, A. S. J. Am. Chem. Soc. 2004, 126, 1503-1517.
48. Lide, D. R. Handbook of Chemistry and Physics, 85th ed.; CRC Press, Boca Raton, FL, 2004-2005; Section 8, p 141.
49. Arduengo, A. J. III; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. J.; Unverzagt, M. Tetrahedron 1999, 55, 14523-14534.
50. Kuhn, N.; Kratz, T. Synthesis 1993, 561-562.