N-substituted guanidinate anions as ancillary ligands in organolanthanide chemistry. Synthesis and characterization of {CyNC[N(SiMe3)2]NCy}2SmCH(SiMe 3)2

Organometallics

Volumn 17, Issue 20, 1998, Pages 4387-4391

  Zhou, Yuanlin ^a   Yap, Glenn P A ^a   Richeson, Darrin S ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001449145     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980480r     Document Type: Article

References (52)

1. For general organolanthanide reviews, see: (a) Schumann, H.; Meese-Marktschffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865 and references therein, (b) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. S., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2 and references therein, (b) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283 and references therein. (c) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131 and references therein. (d) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneider, K. A., Eyring, L., Eds.; Elsevier: Amsterdam, 1984; Chapter 50. (e) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. S., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21 and references therein.
2. For general organolanthanide reviews, see: (a) Schumann, H.; Meese-Marktschffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865 and references therein, (b) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. S., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2 and references therein, (b) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283 and references therein. (c) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131 and references therein. (d) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneider, K. A., Eyring, L., Eds.; Elsevier: Amsterdam, 1984; Chapter 50. (e) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. S., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21 and references therein.
3. For general organolanthanide reviews, see: (a) Schumann, H.; Meese-Marktschffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865 and references therein, (b) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. S., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2 and references therein, (b) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283 and references therein. (c) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131 and references therein. (d) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneider, K. A., Eyring, L., Eds.; Elsevier: Amsterdam, 1984; Chapter 50. (e) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. S., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21 and references therein.
4. For general organolanthanide reviews, see: (a) Schumann, H.; Meese-Marktschffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865 and references therein, (b) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. S., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2 and references therein, (b) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283 and references therein. (c) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131 and references therein. (d) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneider, K. A., Eyring, L., Eds.; Elsevier: Amsterdam, 1984; Chapter 50. (e) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. S., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21 and references therein.
5. For general organolanthanide reviews, see: (a) Schumann, H.; Meese-Marktschffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865 and references therein, (b) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. S., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2 and references therein, (b) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283 and references therein. (c) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131 and references therein. (d) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneider, K. A., Eyring, L., Eds.; Elsevier: Amsterdam, 1984; Chapter 50. (e) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. S., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21 and references therein.
6. For general organolanthanide reviews, see: (a) Schumann, H.; Meese-Marktschffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865 and references therein, (b) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. S., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2 and references therein, (b) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283 and references therein. (c) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131 and references therein. (d) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneider, K. A., Eyring, L., Eds.; Elsevier: Amsterdam, 1984; Chapter 50. (e) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. S., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21 and references therein.
7. For examples of catalytic activity of organolanthanides in a variety of alkene and alkyne transformations including hydrogenation see: (a) Molander, G. A.; Hoberg, J. O. J. Org. Chem. 1992, 57, 3266. (b) Jeske, G.; Lauke, H.; Mauermann, H.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8111. (c) Evans, W. J.; Bloom, I.; Hunter, W. E.; Atwood, J. L. J. Am. Chem. Soc. 1983, 105, 1401.
8. For examples of catalytic activity of organolanthanides in a variety of alkene and alkyne transformations including hydrogenation see: (a) Molander, G. A.; Hoberg, J. O. J. Org. Chem. 1992, 57, 3266. (b) Jeske, G.; Lauke, H.; Mauermann, H.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8111. (c) Evans, W. J.; Bloom, I.; Hunter, W. E.; Atwood, J. L. J. Am. Chem. Soc. 1983, 105, 1401.
9. For examples of catalytic activity of organolanthanides in a variety of alkene and alkyne transformations including hydrogenation see: (a) Molander, G. A.; Hoberg, J. O. J. Org. Chem. 1992, 57, 3266. (b) Jeske, G.; Lauke, H.; Mauermann, H.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8111. (c) Evans, W. J.; Bloom, I.; Hunter, W. E.; Atwood, J. L. J. Am. Chem. Soc. 1983, 105, 1401.
10. For examples of catalytic activity of organolanthanides in hydroamination see: (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295. (b) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770. (c) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118. 707. (d) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275. (e) Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716. (f) Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108.
11. For examples of catalytic activity of organolanthanides in hydroamination see: (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295. (b) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770. (c) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118. 707. (d) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275. (e) Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716. (f) Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108.
12. For examples of catalytic activity of organolanthanides in hydroamination see: (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295. (b) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770. (c) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118. 707. (d) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275. (e) Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716. (f) Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108.
13. For examples of catalytic activity of organolanthanides in hydroamination see: (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295. (b) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770. (c) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118. 707. (d) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275. (e) Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716. (f) Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108.
14. For examples of catalytic activity of organolanthanides in hydroamination see: (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295. (b) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770. (c) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118. 707. (d) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275. (e) Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716. (f) Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108.
15. For examples of catalytic activity of organolanthanides in hydroamination see: (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295. (b) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770. (c) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118. 707. (d) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275. (e) Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716. (f) Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108.
16. For examples of catalytic activity of organolanthanides in hydrosilylation see: (a) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157. (b) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347. (c) Sakakura, T.; Lautenschlager, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1991, 40. (d) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. J. J. Am. Chem. Soc. 1991, 113, 8564.
17. For examples of catalytic activity of organolanthanides in hydrosilylation see: (a) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157. (b) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347. (c) Sakakura, T.; Lautenschlager, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1991, 40. (d) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. J. J. Am. Chem. Soc. 1991, 113, 8564.
18. For examples of catalytic activity of organolanthanides in hydrosilylation see: (a) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157. (b) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347. (c) Sakakura, T.; Lautenschlager, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1991, 40. (d) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. J. J. Am. Chem. Soc. 1991, 113, 8564.
19. For examples of catalytic activity of organolanthanides in hydrosilylation see: (a) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157. (b) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347. (c) Sakakura, T.; Lautenschlager, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1991, 40. (d) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. J. J. Am. Chem. Soc. 1991, 113, 8564.
20. For examples of catalytic activity of organolanthanides in hydroboration see: (a) Bijpost, E. A.; Duchateau, R.; Teuben, J. H. J. Mol. Catal. 1995, 95, 121. (b) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
21. For examples of catalytic activity of organolanthanides in hydroboration see: (a) Bijpost, E. A.; Duchateau, R.; Teuben, J. H. J. Mol. Catal. 1995, 95, 121. (b) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
22. For examples of catalytic activity of organolanthanides in polymerization see: (a) Heeres, H. J.; Renkema, J.; Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1988, 7, 2495. (b) Jeske, G.; Schock, L. E.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8103. (c) Evans, W. J.; DeCoster, P. M.; Greaves, J. Macromolecules 1995, 28, 7929. (d) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (e) Boff. L. S.; Novak, B. M. Macromolecules 1997, 30, 3494.
23. For examples of catalytic activity of organolanthanides in polymerization see: (a) Heeres, H. J.; Renkema, J.; Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1988, 7, 2495. (b) Jeske, G.; Schock, L. E.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8103. (c) Evans, W. J.; DeCoster, P. M.; Greaves, J. Macromolecules 1995, 28, 7929. (d) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (e) Boff. L. S.; Novak, B. M. Macromolecules 1997, 30, 3494.
24. For examples of catalytic activity of organolanthanides in polymerization see: (a) Heeres, H. J.; Renkema, J.; Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1988, 7, 2495. (b) Jeske, G.; Schock, L. E.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8103. (c) Evans, W. J.; DeCoster, P. M.; Greaves, J. Macromolecules 1995, 28, 7929. (d) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (e) Boff. L. S.; Novak, B. M. Macromolecules 1997, 30, 3494.
25. For examples of catalytic activity of organolanthanides in polymerization see: (a) Heeres, H. J.; Renkema, J.; Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1988, 7, 2495. (b) Jeske, G.; Schock, L. E.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8103. (c) Evans, W. J.; DeCoster, P. M.; Greaves, J. Macromolecules 1995, 28, 7929. (d) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (e) Boff. L. S.; Novak, B. M. Macromolecules 1997, 30, 3494.
26. For examples of catalytic activity of organolanthanides in polymerization see: (a) Heeres, H. J.; Renkema, J.; Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1988, 7, 2495. (b) Jeske, G.; Schock, L. E.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8103. (c) Evans, W. J.; DeCoster, P. M.; Greaves, J. Macromolecules 1995, 28, 7929. (d) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (e) Boff. L. S.; Novak, B. M. Macromolecules 1997, 30, 3494.
27. For examples of catalytic activity of organolanthanides in reductive cyclizations see: (a) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415. (b) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123.
28. For examples of catalytic activity of organolanthanides in reductive cyclizations see: (a) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415. (b) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123.
29. Wilkinson, G.; Birmingham, J. M. J. Am. Chem. Soc. 1954, 76, 6210.
30. Mehrotra, R. C. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D.; McCleverty, J. A., Eds.; Pergamon Press: Oxford, U.K., 1987; Chapter 13.8.
31. Kilner, M.; Baker, J. Coord. Chem. Rev. 1994, 133, 219.
32. Moore, D. S.; Robinson, S. D. Adv. Inorg. Chem. Radiochem. 1986, 30, 1.
33. (a) Hagen, C.; Reddmann, H.; Amberger, H.-D.; Edelmann, F. T.; Pegelow, U.; Shalimoff, G. V.; Edelstein, N. M. J. Organomet. Chem. 1993, 462, 69.
34. (b) Wedler, M.; Knosel, F.; Pieper, U.; Stalke, D.; Edelmann, F. T.; Amberger, H.-D. Chem. Ber. 1992, 125, 2171.
35. Recknagel, A.: Knosel, F.; Gornitzka, H.; Noltemeyer, M.; Edelmann, F. T.; Behrens, U. J. Organomet. Chem. 1991, 417, 363.
36. (a) Wedler, M.; Noltemeyer, M.; Pieper, U.; Schmidt, H.-G.; Stalke, D.; Edelmann, F. T. Angew. Chem., Int. Ed. Engl. 1990, 29, 894.
37. (b) Wedler, M.; Recknagel, A.; Gilje, J. W.; Noltemeyer, M.; Edelmann, F. T. J. Organomet. Chem. 1992, 426, 295.
38. (a) Duchateau, R.; van Wee, C. T.; Meetsma, A.; van Duijnen, P. T.; Teuben, J. H. Organometallics 1996, 15, 2279.
39. (b) Duchateau, R.; van Wee, C. T.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc 1993, 115, 4931.
40. (a) Foley, S. R.; Bensimon, C.; Richeson, D. S. J. Am. Chem. Soc. 1997, 119, 10359 and references therein,
41. (b) Littke, A.; Sleiman, N.; Bensimon, C.; Richeson, D.; Yap, G. P. A.; Brown, S. Organometallics 1998, 17, 446 and references therein.
42. (a) Coles, M. P.; Jordan R. F. J. Am. Chem. Soc. 1997, 119, 8125.
43. (b) Coles, M. P.; Swenson, D. C.; Jordan, R. F.; Young, V. G. Organometallics 1997, 16, 5183.
44. 2 = 1.061.
45. 2) = 0.102.
46. For conciseness, the discussion of the structural parameters of 7 and the ORTEP shown in Figure 1 are confined to one of the three molecules that constitute the asymmetric unit in the crystal structure. Full data are provided in the Supporting Information.
47. (a) Schumann, H.; Rosenthal, E. C. E.; Kociok-Kohn, G.; Molander, G. A.; Winterfeld, J. J. Organomet. Chem. 1995, 496, 233.
48. (b) Clark, D. L.; Gordon, J. C.; Huffman, J. C.; Watkin, J. G.; Zwick, B. D. Organometallics 1994, 13, 4266.
49. (c) Giardello, M. A.; Conticello, V. P.; Brard, L.; Sabat, M.; Rheingold, A. L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10212.
50. (d) Conticello, V. P.; Brard, L.; Giardello, M. A.; Tsuji, Y.; Sabat, M.; Stern, C. L.; Marks T. J. J. Am. Chem. Soc. 1992, 114, 2761.
51. (e) Hitchcock, P. B.; Lappert, M. F.; Smith, R. G. J. Chem. Soc., Chem. Commun. 1989, 369.
52. (f) Hitchcock, P. B.; Lappert, M. F.; Smith, R. G.; Bartlett, R. A.; Power, P. P. J. Chem. Soc., Chem. Commun. 1988, 1007.