Lewis acid trapping of an elusive copper-tosylnitrene intermediate using scandium triflate

Journal of the American Chemical Society

Volumn 134, Issue 36, 2012, Pages 14710-14713

  Kundu, Subrata ^a   Miceli, Enrico ^a   Farquhar, Erik ^b   Pfaff, Florian Felix ^a   Kuhlmann, Uwe ^c   Hildebrandt, Peter ^c   Braun, Beatrice ^a   Greco, Claudio ^a   Ray, Kallol ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

^b CASE WESTERN RESERVE UNIVERSITY   (United States)

^c TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION REACTION; AZIRIDINATION; LEWIS ACID; OXIDATION CATALYSIS; RESONANCE RAMAN; SCANDIUM TRIFLATE; X-RAY ABSORPTION NEAR EDGE SPECTROSCOPY;

CATALYSIS; ELECTRONIC STRUCTURE; NUCLEAR MAGNETIC RESONANCE; REACTION INTERMEDIATES; SCANDIUM;

COPPER;

COPPER; CYCLOHEXANE; LEWIS ACID; NITRO DERIVATIVE; SCANDIUM; SCANDIUM TRIFLATE; TOSYLNITRENE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; QUANTUM YIELD; RAMAN SPECTROMETRY; REACTION ANALYSIS; THERMOSTABILITY; TOSYLAMINATION; X RAY ABSORPTION NEAR EDGE SPECTROSCOPY; X RAY ABSORPTION SPECTROSCOPY;

COPPER; IMINES; LEWIS ACIDS; MESYLATES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SCANDIUM; TOSYL COMPOUNDS;

EID: 84866390222     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja306674h     Document Type: Article

References (33)

1. Kwart, H.; Kahn, A. A. J. Am. Chem. Soc. 1967, 89, 1950
2. Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905
3. Diaz-Requejo, M. M.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Perez, P. J. J. Am. Chem. Soc. 2003, 125, 12078
4. Fructos, M. R.; Trofimenko, S.; Diaz-Requejo, M. M.; Perez, P. J. J. Am. Chem. Soc. 2006, 128, 11784
5. Badiei, Y. M.; Dinescu, A.; Dai, X.; Palomino, R. M.; Heinemann, F. W.; Cundari, T. R.; Warren, T. H. Angew. Chem., Int. Ed. 2008, 47, 9961
6. Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889
7. Diaz-Requejo, M. M.; Perez, P. J.; Brookhart, M.; Templeton, J. L. Organometallics 1997, 16, 4399
8. King, E. R.; Hennesy, E. T.; Betley, T. A. J. Am. Chem. Soc. 2011, 133, 4917
9. Lyaskovskyy, V.; Suarez, A. I. O.; Lu, H.; Jiang, H.; Zhang, X. P.; de Bruin, B. J. Am. Chem. Soc. 2011, 133, 12264
10. Waterman, R.; Hillhouse, G. L. J. Am. Chem. Soc. 2008, 130, 12628
11. Brandt, P.; Södergren, M. J.; Andersson, P. G.; Norrby, P.-O. J. Am. Chem. Soc. 2000, 122, 8013
12. Gillespie, K. M.; Crust, E. J.; Deeth, R. J.; Scott, P. Chem. Commun. 2001, 785
13. Tekarli, S. M.; Williams, T. G.; Cundari, T. R. J. Chem. Theory Comput. 2009, 5, 2959
14. Cundari, T. R.; Dinescu, A.; Kazi, A. B. Inorg. Chem. 2008, 47, 10067
15. Liang, H.-C.; Zhang, C. X.; Henson, M. J.; Sommer, R. D.; Hatwell, K. R.; Kaderli, S.; Zuberbühler, A. D.; Rheingold, A. L.; Solomon, E. I.; Karlin, K. D. J. Am. Chem. Soc. 2002, 124, 4170
16. Macikenas, D.; Skrzypczak-Jankun, E.; Protasiewicz, J. D. J. Am. Chem. Soc. 1999, 121, 7164
17. Gonzalez-Alvarez, M.; Alzuet, G.; Borras, J.; Agudo, L. C.; Garcia-Granda, S.; Bernardo, J. M. M. J. Inorg. Biochem. 2004, 98, 189
18. Macias, B.; Villa, M. V.; Gomez, B.; Borras, J.; Alzuet, G.; Gonzalez-Alvarez, M.; Castineiras, A. J. Inorg. Biochem. 2007, 101, 444
19. Que, L., Jr. Physical Methods in Bioinorganic Chemistry: Spectroscopy and Magnetism; University Science Books: Sausalito, CA, 2000.
20. Pfaff, F. F.; Kundu, S.; Risch, M.; Pandian, S.; Heims, F.; Pryjomska-Ray, I.; Haack, P.; Metzinger, R.; Bill, E.; Dau, H.; Comba, P.; Ray, K. Angew. Chem., Int. Ed. 2011, 50, 1711
21. 2+ (0%), which follows the order of decreasing Lewis acidity of the metal ions. See: Fukuzumi, S.; Ohkubo, K. J. Am. Chem. Soc. 2002, 124, 10270
22. Donoghue, P. J.; Tehranchi, J.; Cramer, C. J.; Sarangi, R.; Solomon, E. I.; Tolman, W. B. J. Am. Chem. Soc. 2011, 133, 17602
23. King, A. E.; Huffman, L. M.; Casitas, A.; Costas, M.; Ribas, X.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 12068
24. Fukuzumi, S.; Morimoto, Y.; Kotani, H.; Naumov, P.; Lee, Y.-M.; Nam, W. Nat. Chem. 2010, 2, 756
25. Kau, L. S.; Spira-Solomon, D. J.; Penner-Hahn, J. E.; Hodgson, K. O.; Solomon, E. I. J. Am. Chem. Soc. 1987, 109, 6433
26. DuBois, J. L.; Mukherjee, P.; Stack, T. D. P.; Hedman, B.; Solomon, E. I.; Hodgson, K. O. J. Am. Chem. Soc. 2000, 122, 5775
27. Lu, C. C.; George, S. D.; Weyhermüller, T.; Bill, E.; Bothe, E.; Wieghardt, K. Angew. Chem., Int. Ed. 2008, 47, 6384
28. Luo, Y.-R. Comprehensive Handbook of Chemical Bond Energies; CRC Press: Boca Raton, FL, 2007.
29. Yoshizawa, K.; Kihara, N.; Kamachi, T.; Shiota, Y. Inorg. Chem. 2006, 45, 3034
30. Crespo, A.; Marti, M. A.; Roitberg, A. E.; Amzel, L. M.; Estrin, D. A. J. Am. Chem. Soc. 2006, 128, 12817
31. Hong, S.; Huber, S. M.; Gagliardi, L.; Cramer, C. C.; Tolman, W. B. J. Am. Chem. Soc. 2007, 129, 14190
32. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047
33. Himes, R. A.; Karlin, K. D. Curr. Opin. Chem. Biol. 2009, 13, 119