Rapid injection NMR in mechanistic organocopper chemistry. Preparation of the elusive copper(III) intermediate

Journal of the American Chemical Society

Volumn 129, Issue 23, 2007, Pages 7208-7209

  Bertz, Steven H ^a,b   Cope, Stephen ^a   Murphy, Michael ^a   Ogle, Craig A ^a   Taylor, Brad J ^a  

^a UNIVERSITY OF NORTH CAROLINA AT CHARLOTTE   (United States)

^b Complexity Study Center ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; CHLOROTRIMETHYLSILANE; COPPER; GILMAN REAGENT; LITHIUM CYANOBIS(METHYL)(3 TRIMETHYLSILOXYCYCLOHEX 2 EN 1 YL)CUPRATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; INJECTION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROMETER;

EID: 34250796928     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067533d     Document Type: Article

References (37)

1. Part 3 of a series; for part 2, see ref 17. For part 1, see ref 20. This paper is also part 34 of the SHB series, New Copper Chemistry. For part 33, see ref 17. For part 32, see ref 18. For part 31, see Bertz, S. H.; Ogle, C. A.; Rastogi, A. J. Am. Chem. Soc. 2005, 127, 1372-3.
2. Gilman, H.; Jones, R. G.; Woods, L. A. J. Org. Chem. 1952, 17, 1630-4.
3. House, H. O. Acc. Chem. Res. 1976, 9, 59-67.
4. House, H. O.; Respess, W. L.; Whitesides, G. M. J. Org. Chem. 1966, 31, 3128-41.
5. Whitesides, G. M.; Fischer, W. F.; San Filippo, J.; Bashe, R. W.; House, H. O. J. Am. Chem. Soc. 1969, 91, 4871-82.
6. Corey, E. J.; Posner, G. H. J. Am. Chem. Soc. 1968, 90, 5615-6.
7. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6019-22.
8. Posner, G. H. Studies in Organometallic Chemistry. Ph.D. Dissertation, Harvard University, Cambridge, MA, 1968, pp 57-60.
9. Posner, G. H. Org. React. 1972, 19, 1-113.
10. Posner, G. H. Org. React. 1975, 22, 253-400.
11. Modern Organocopper Chemistry: Krause, N., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
12. Goering, H. L.; Kantner, S. S.; Seitz, E. P. J. Org. Chem. 1985, 50, 5495-9.
13. Krauss, S. R.; Smith, S. G. J. Am. Chem. Soc. 1981, 103, 141-8.
14. Bertz, S. H.; Dabbagh, G.; Cook, J. M.; Honkan, V. J. Org. Chem. 1984, 49, 1739-43.
15. Johnson, C. R.; Dutra, G. A. J. Am. Chem. Soc. 1973, 95, 7783-8.
16. Bertz, S. H.; Dabbagh, G.; Mujsce, A. M. J. Am. Chem. Soc. 1991, 113, 631-6.
17. Murphy, M. D.; Ogle, C. A.; Bertz, S. H. Chem. Commun. 2005, 854-6.
18. Bertz, S. H.; Human, J.; Ogle, C. A.; Seagle, P. Org. Biomol. Chem. 2005, 3, 392-4.
19. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; p 686.
20. Bertz, S. H.; Carlin, C. M.; Deadwyler, D. A.; Murphy, M. D.; Ogle, C. A.; Seagle, P. H. J. Am. Chem. Soc. 2002, 124, 13650-1.
21. Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11025-6.
22. Hu, H.; Snyder, J. P. J. Am. Chem. Soc. 2007, 129, 7210-11.
23. Hallnemo, G.; Olsson, T.; Ullenius, C. J. Organomet. Chem. 1984, 265, C22-4.
24. Bertz, S. H.; Smith, R. A. J. J. Am. Chem. Soc. 1989, 111, 8276-7.
25. +: (a) Boche, G.; Bosold, F.; Marsch, M.; Harms, K. Angew. Chem., Int. Ed. 1998, 37, 1684-6.
26. (b) Kronenburg, C. M. P.; Jastrzebski, J. T. B. H.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1998, 120, 9688-9.
27. Melník, M.; Kabešová, M. J. Coord. Chem. 2000, 50, 323-38.
28. Eujen, R.; Hoge, B.; Brauer, D. J. J. Organomet. Chem. 1996, 519, 7-20.
29. (a) Willert-Porada, M. A.; Burton, D. J.; Baenziger, N. C. J. Chem. Soc. Chem. Commun. 1989, 1633-4.
30. (b) Naumann, D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1482-3.
31. Furuta, H.; Maeda, H.; Osuka, A. J. Am. Chem. Soc. 2000, 122, 803-7.
32. Ribas, X.; Jackson, D. A.; Donnadieu, B.; Mahía, J.; Parella. T.; Xifra, R.; Hedman, B.; Hodgson, K. O.; Llobet, A.; Stack, T. D. P. Angew. Chem., Int. Ed. 2002, 41, 2991-4.
33. Varadarajan, A.; Johnson, S. E.; Gomez, F. A.; Chakrabarti, S.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 9003-11.
34. Bertz, S. H. J. Am. Chem. Soc. 1990, 112, 4031-2.
35. Bertz, S. H. J. Am. Chem. Soc. 1991, 113, 5470-1.
36. 29Si NMR, 12.68 ppm. Without the TMS group, a Cu(III) intermediate was not observed.
37. Carty, A. J.; Jacobson, S. E. J. Chem. Soc., Chem. Commun. 1975, 175-6.