Nitrogen transfer from a nitridomanganese(V) complex: Amination of silyl enol ethers

Journal of the American Chemical Society

Volumn 118, Issue 4, 1996, Pages 915-916

  Du Bois, J ^a   Hong, Jason ^a   Carreira, Erick M ^b   Day, Michael W ^b  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344218074     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953659r     Document Type: Article

References (39)

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11. For metal-catalyzed azindination with PhI=NTs, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742 and references therein. (b) Li, Z.; Quan, R.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889 and references therein. (c) Noda, K.; Hosoya, N.; Irie, R.; Ito, Y.; Katsuki, T. Synlett 1993, 469. (d) O'Connor, K.; J.; Wey, S.-J ; Burrows, C J. Tetrahedron Lett. 1992, 33, 1001.
12. For metal-catalyzed azindination with PhI=NTs, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742 and references therein. (b) Li, Z.; Quan, R.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889 and references therein. (c) Noda, K.; Hosoya, N.; Irie, R.; Ito, Y.; Katsuki, T. Synlett 1993, 469. (d) O'Connor, K.; J.; Wey, S.-J ; Burrows, C J. Tetrahedron Lett. 1992, 33, 1001.
13. For metal-catalyzed azindination with PhI=NTs, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742 and references therein. (b) Li, Z.; Quan, R.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889 and references therein. (c) Noda, K.; Hosoya, N.; Irie, R.; Ito, Y.; Katsuki, T. Synlett 1993, 469. (d) O'Connor, K.; J.; Wey, S.-J ; Burrows, C J. Tetrahedron Lett. 1992, 33, 1001.
14. For metal-catalyzed azindination with PhI=NTs, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742 and references therein. (b) Li, Z.; Quan, R.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889 and references therein. (c) Noda, K.; Hosoya, N.; Irie, R.; Ito, Y.; Katsuki, T. Synlett 1993, 469. (d) O'Connor, K.; J.; Wey, S.-J ; Burrows, C J. Tetrahedron Lett. 1992, 33, 1001.
15. For a review on available aziridination and amination methods, see: Kemp, J. E. G. In Comprehensive Organic Synthesis; Ley, S. V., Ed.; Pergamon Oxford, U.K., 1991; Vol. 7, p. 469 See also: Vedejs, E., Sano, H. Tetrahedron Lett. 1992, 33, 3261.
16. For a review on available aziridination and amination methods, see: Kemp, J. E. G. In Comprehensive Organic Synthesis; Ley, S. V., Ed.; Pergamon Oxford, U.K., 1991; Vol. 7, p. 469 See also: Vedejs, E., Sano, H. Tetrahedron Lett. 1992, 33, 3261.
17. For a review of nitrido metal complexes, see (a) Dehnicke, K.; Strahle, J. Angew. Chem., Int. Ed. Engl. 1992, 31, 955. (b) Nugent, W. A.; Haymore, B. L. Coord. Chem. Rev. 1980, 31, 123 See also: Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds: Wiley-Interscience New York, 1988.
18. For a review of nitrido metal complexes, see (a) Dehnicke, K.; Strahle, J. Angew. Chem., Int. Ed. Engl. 1992, 31, 955. (b) Nugent, W. A.; Haymore, B. L. Coord. Chem. Rev. 1980, 31, 123 See also: Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds: Wiley-Interscience New York, 1988.
19. For a review of nitrido metal complexes, see (a) Dehnicke, K.; Strahle, J. Angew. Chem., Int. Ed. Engl. 1992, 31, 955. (b) Nugent, W. A.; Haymore, B. L. Coord. Chem. Rev. 1980, 31, 123 See also: Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds: Wiley-Interscience New York, 1988.
20. Salen = N,N′-ethylenebis(salicylideneaminato); saltmen = N,N′-(1.1.2.2-tetramethylethylene)bis(salicylideneaminato).
21. (a) Groves, J. T.; Takahashi, T. J Am. Chem. Soc. 1983, 105, 2074.
22. (b) Groves, J. T.; Takahashi, T.; Butler, W M. Inorg. Chem. 1983, 22, 884.
23. Arshankow, S. I.; Poznjak, A. L. Z. Anorg. Allg. Chem. 1981, 481, 201. (Salen)Cr(N) has also been prepared by intermetal nitrogen atom transfer from a nitrido(octaethylporphyrinato)chromium to (salen)CrCl: Neely, F. L.: Bottomley, L. A. Inorg. Chim. Acta 1992, 192, 147.
24. Arshankow, S. I.; Poznjak, A. L. Z. Anorg. Allg. Chem. 1981, 481, 201. (Salen)Cr(N) has also been prepared by intermetal nitrogen atom transfer from a nitrido(octaethylporphyrinato)chromium to (salen)CrCl: Neely, F. L.: Bottomley, L. A. Inorg. Chim. Acta 1992, 192, 147.
25. 3: Che, C.-M.; Ma, J.-X., Wong, W -T ; Lai, T.-F.; Poon, C.-K. Inorg. Chem 1988, 27, 2547
26. (a) Buchler, J. W.; Dreher, C., Lay, K -L. Z. Naturforsch., B. Anorg. Chem.. Org. Chem 1982, 37B, 1155.
27. (b) Buchler, J. W.; Dreher, C., Lay, K.-L., Lee, Y. J. A.: Scheidt, W R Inorg. Chem 1983, 22, 888.
28. Hill, C. L., Hollander, F. J. J. Am Chem. Soc. 1982, 104, 7318.
29. For the preparation of 2,3-diamino-2,3-dimethylbutane. see. Sayre, R. J. Am. Chem. Soc 1955, 77, 6689.
30. The nature of this dark brown Mn(III) species has not been established For an analogous reaction in which the resulting Mn(III)-salen complex was isolated and characterized following treatment with LiCl, see. Zhang, W., Jacobsen, E. N J. Org Chem 1991, 56, 2296
31. 2-saltmen and 2 is provided in the supporting information
32. merge = 1.05). The structure was solved by direct methods (SHELXS-86) and refined ansiotropically (SHELXL-93) to R = 0.061 with GOF = 1.304. Additional information is given in the supporting information.
33. A Mn-N distance of 1.51 Å has been reported for the (5,15-dimethyl-2,3,7,8,12,13,17,18-octaethyl-5H, 15H-porphyrinato)nitridomanganese(V) compound, see ref 11b.
34. The preparation of a nitrido-Mn(V) phthalocyanine complex has been reported; however, its structure was only established by UV and resonance Raman spectroscopy. Grunewald, H.; Homborg, H. Z. Anorg. Allg. Chem. 1992, 608, 81. A stable Mn(V) oxo complex has been crystallographically characterized, see: Collins, T. J.; Powell, R. D.; Slebodnick, C., Uffelman, E. S. J. Am. Chem. Soc. 1990, 112, 899.
35. The preparation of a nitrido-Mn(V) phthalocyanine complex has been reported; however, its structure was only established by UV and resonance Raman spectroscopy. Grunewald, H.; Homborg, H. Z. Anorg. Allg. Chem. 1992, 608, 81. A stable Mn(V) oxo complex has been crystallographically characterized, see: Collins, T. J.; Powell, R. D.; Slebodnick, C., Uffelman, E. S. J. Am. Chem. Soc. 1990, 112, 899.
36. 2O/ethylene glycol-dry ice) and only a catalytic amount of pyridine (62 μmol) was employed.
37. 13C NMR, IR) to authentic material which was prepared according to a known procedure for a related compound: Chittenden, R. A.; Cooper, G. H J. Chem Soc. C, 1970, 49.
38. For mechanistic studies on the reaction of TFAA with nitrido-Cr and Mn porphyrin complexes, see: (a) Bottomley, L. A.; Neely, F. L. Inorg Chem. 1990, 29, 1860. (b) Bottomley, L. A.; Neely, F. L. J. Am. Chem. Soc. 1988, 110, 6748.
39. For mechanistic studies on the reaction of TFAA with nitrido-Cr and Mn porphyrin complexes, see: (a) Bottomley, L. A.; Neely, F. L. Inorg Chem. 1990, 29, 1860. (b) Bottomley, L. A.; Neely, F. L. J. Am. Chem. Soc. 1988, 110, 6748.