Hydroamination of alkynes catalyzed by a titanium pyrrolyl complex

Organometallics

Volumn 20, Issue 24, 2001, Pages 5011-5013

  Cao, Changsheng ^a   Ciszewski, James T ^a   Odom, Aaron L ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROAMINATION; REGIOSELECTIVITY; TITANIUM PYRROLYL COMPLEX;

AMINATION; CATALYSIS; CATALYSTS; HIGH TEMPERATURE EFFECTS; MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL); TITANIUM COMPOUNDS;

ORGANOMETALLICS;

EID: 0035956451     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010595m     Document Type: Article

References (49)

1. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281.
2. Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Müller, T. E.; Zapf, A. J. Organomet. Chem. 1998, 566, 277-285.
3. (b) Yamamoto, Y.; Radhakrishnan, U. Chem. Soc. Rev. 1999, 28, 199-207.
4. For some leading examples of late-transition-metal-catalyzed hydroamination (a) Kadota, I.; Shibuya, A.; Lutete, L. M.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4570-4571.
5. (b) Weber, L.; Barlmeyer, M.; Quasdorff, J.-M.; Sievers, H. L.; Stammler, H.-G.; Neumann, B. Organometallics 1999, 18, 2497-2504.
6. (c) Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1999, 38, 3222-3223.
7. (d) Müller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A. K.; Walter, E.; Yan, Y.-K. Organometallics 2000, 19, 170-183.
8. (e) Beller, M.; Thiel, O. R.; Trauthwein, H.; Hartung, C. G. Chem. Eur. J. 2000, 6, 2513-2522.
9. (f) Burling, S.; Field, L. D.; Messerle, B. A. Organometallics 2000, 19, 87-90.
10. (g) Kawatsura; M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546-9547.
11. Early-metal examples include: (a) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305-2308.
12. (b) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923-2924.
13. (c) Kim, Y. K.; Livinghouse, T.; Bercaw, J. E. Tetrahedron Lett. 2001, 42, 2933-2935.
14. (d) Haak, E.; Siebeneicher, H.; Doye, S. Org. Lett. 2000, 2, 1935-1937.
15. (e) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389-3391.
16. (f) Siebeneicher, H.; Doye, S. J. Prak. Chem.-Chem. Ztg. 2000, 342, 102-106.
17. (g) McCrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11589.
18. (h) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719.
19. (i) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763.
20. For leading examples of Ln-catalyzed hydroamination, see: (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757-1771.
21. (b) Molander, G. A.; Dowdy, E. D. J. Org. Chem. 1999, 64, 6515-6517.
22. (c) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757-1771.
23. (d) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770-3772.
24. (a) Haskel, A.; Straub, T.; Eisen, M. S. Organometallics 1996, 15, 3773-3775.
25. (b) Straub, T.; Frank, W.; Reiss, G. J.; Eisen, M. S. J. Chem. Soc., Dalton Trans. 1996, 2541-2546.
26. For ancillary ligand effects within Cp-based systems, see: (a) Tian, S.; Arrendondo, V. M.; Stern, C. L.; Marks, T. J. Organometallics 1999, 18, 2568-2570.
27. (b) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705-4711. See also ref 3a,b.
28. For use of hexamethyldisilazide lanthanide complexes in hydroamination catalysis, see: (a) Bürgstein, M. R.; Berberich, H.; Roesky, P. W. Chem. Eur. J. 2001, 7, 3078-3085.
29. For (aminotroponiminate)yttrium amido hydroamination catalysis, see: (b) Bürgstein, M. R.; Berberich, H.; Roesky, P. W. Organometallics 1998, 17, 1452-1454.
30. Raines, S.; Kovacs, C. A. J. Heterocycl. Chem. 1970, 7, 223.
31. Harris, S. A.; Ciszewski, J. T.; Odom, A. L. Inorg. Chem. 2001, 40, 1987-1988.
32. Bradley, D. C.; Thomas, I. M. J. Chem. Soc. 1960, 3859.
33. For other recently described titanium pyrrolyl complexes, see: (a) Huang, J.-H.; Chi, L.-S. Huang, F.-M.; Kuo, P.-C.; Zhou, C.-C.; Lee, G.-H.; Peng, S.-M. J. Chin. Chem. Soc. 2000, 47, 895.
34. (b) Yoshida, Y.; Matsui, S.; Takagi, Y.; Mitani, M.; Nitabaru, M.; Nakano, T.; Tanaka, H.; Fujita, T. Chem. Lett. 2000, 1270-1271.
35. (c) Drevs, H.; Schmeiber, A.; Hartung, H.; Baumeister, U. Chem. Ber. 1996, 129, 853-857.
36. Yanhui, S.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 3967-3969.
37. tN=C(Me)Ph, the imines were prepared and yields obtained directly versus dodecane internal standard.
38. A 1% yield of either product can readily be observed by GC. In cases where only one product is observed, we conservatively estimate the selectivity as 50:1.
39. A possible explanation for the selectivities in this reaction involves synthesis of a metallocyclobutane intermediate due to a 1,3-hydrogen shift. Trösch, D. J. M.; Collier, P. E.; Bashall, A.; Gade, L. H.; McPartlin, M.; Mountford, P.; Radojevic, S. Organometallics 2001, 20, 3308-3313.
40. 13C NMR, and mass spectrometry. The reaction yielded 3.5 g (46%) of purified compound.
41. For other early-transition-metal cyclotrimerizations of alkynes, see: (a) Strickler, J. R.; Bruck, M. A.; Wigley, D. E. J. Am. Chem. Soc. 1990, 112, 2814-2816.
42. (b) Smith, D. P.; Strickler, J. R.; Gray, S. D.; Bruck, M. A.; Holmes, R. S.; Wigley, D. E. Organometallics 1992, 11, 1275-1288.
43. (c) Hartung, J. B.; Pedersen, S. F. Organometallics 1990, 9, 1414-1417.
44. 4 and the solvent was removed in vacuo. To the residue was added 50 mL of pentane. Cooling to -25°C caused p-toluidine to crystallize, which was removed by filtration. The product was distilled (65-67°C, 0.25 mmHg) to give pure 9.4 g (82%) of 2-(p-tolylamino)hexane.
45. For a few examples of catalytic asymmetric hydrogenation of imines, see: (a) Sablong, R.; Osborn, J. A. Tetrahedron Lett. 1996, 37, 4937-4940.
46. (b) Shnider, P.; Koch, G.; Pretot, R.; Wang, G.; Bohnen, F. M.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887-892.
47. (c) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952-8965.
48. (d) Obora, Y.; Ohta, T.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1997, 119, 3745-3755.
49. Benati, L.; Montevecchi, P. C.; Spagnolo, P. Tetrahedron 1986, 42, 1145-1155.