TiCl4-catalyzed intermolecular hydroamination reactions

Organometallics

Volumn 22, Issue 22, 2003, Pages 4367-4368

  Ackermann, Lutz ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNES; AMINOALLENES; DICHLORIDE; IMIDO COMPLEX; INTERMOLECULAR HYDROAMINATION REACTIONS;

ADDITION REACTIONS; AMINES; CATALYSIS; CATALYSTS; CHLORINE COMPOUNDS; TITANIUM COMPOUNDS;

AMINATION;

EID: 0344493933     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om034143g     Document Type: Article

References (32)

1. (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
2. (b) Nobis, M.; Driessen-Hölscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983-3985.
3. (c) Brunet, J. J.; Neibecker, D. In Catalytic Heterofunctionalization, Togni, A., Grützmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001,; pp 91-141.
4. (d) Roesky, P. W.; Müller, T. E. Angew. Chem., Int. Ed. 2003, 42, 2708-2710.
5. (e) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104-114.
6. (a) Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744.
7. (b) Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108-4109.
8. (c) Beller, M.; Eichberger, M.; Trauthwein, H. Angew. Chem., Int. Ed. 1997, 36, 2225-2227.
9. (d) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366-4367.
10. (e) Kim, Y. K.; Livinghouse, T. Angew. Chem., Int. Ed. 2002, 41, 3645-3647.
11. (f) Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12670-12671.
12. (g) Fadini, L.; Togni, A. Chem. Commun. 2003, 30-31.
13. (h) Utsonomiya, M.; Kuwano, R.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 5608-5609.
14. Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719.
15. (a) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389-3391.
16. (b) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961-1964.
17. Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923-2924.
18. Tillack, A.; Garcia Castro, I.; Hartung, C. G.; Beller, M. Angew. Chem., Int. Ed. 2002, 41, 2541-2543.
19. (a) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967-3969.
20. (b) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011-5013.
21. Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839-2841.
22. Blake, A. J.; Collier, P. E.; Dunn, S. C.; Li, W. S.; Mountford, P.; Shishkin, O. V. J. Chem. Soc., Dalton Trans. 1997, 1549-1558.
23. 3 in intramolecular hydroamination reactions, see: (a) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459-5460.
24. (b) McGrane, P. L.; Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324.
25. Attempts to hydroaminate acyclic 1,3-disubstituted allenes or unfunctionalized alkenes using complex 1 have to date been unsuccessful.
26. 4 itself is ineffective, even as a cyclization catalyst for aminoalkynes: McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489.
27. 2O) under otherwise identical reaction conditions.
28. 1H NMR): tolan and aniline, 81/19; 3-hexyne and aniline, >98/2; tolan and 2,6-dimethylaniline, >98/2; tolan and p-methylaniline, 83/17.
29. A full account will be reported elsewhere: Ackermann, L.; Kaspar, L. T. Unpublished results.
30. For another approach to the indole framework, see: Siebenreicher, H.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 2003, 42, 3042-3044.
31. Titanium-catalyzed anti-Markovnikov hydroamination reactions of terminal alkynes have been reported.
32. For intramolecular hydroamination reactions initiated by a titanium sulfonamido complex, see: Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475-1478.