An ammonia equivalent for the dimethyltitanocene-catalyzed intermolecular hydroamination of alkynes

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1935-1937

  Haak, Edgar ^a   Siebeneicher, Holger ^a   Doye, Sven ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000046807     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006011e     Document Type: Article

References (17)

1. For reviews, see: (a) Taube, R. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, 1996; Vol. 1, pp 507-520.
2. (b) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
3. (c) Müller, T. E.; Beller, M. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 2, pp 316-330.
4. (d) Haak, E.; Doye, S. Chem. Unserer Zeit 1999, 33, 296-303.
5. For catalytic intermolecular hydroaminations of alkynes, see: (a) Barluenga, J.; Aznar, F. Synthesis 1977, 195-196.
6. (b) Barluenga, J.; Aznar, F.; Liz, R.; Rodes, R. J. Chem. Soc., Perkin Trans. 1 1980, 2732-2737.
7. (c) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719.
8. (d) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763.
9. (e) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770-3772.
10. (f) Haskel, A.; Straub, T.; Eisen, M. S. Organometallics 1996, 15, 3773-3775.
11. (g) Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1999, 38, 3222-3225.
12. (h) Tzalis, D.; Koradin, C.; Knochel, P. Tetrahedron Lett. 1999, 40, 6193-6195.
13. (i) See also ref 3.
14. Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389-3391.
15. Benzhydrylamines are usually cleaved more easily than benzylamines: (a) Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: Stuttgart, New York, 1994; pp 220-227.
16. (b) Overman, L. E.; Mendelson, L. T.; Jacobsen, E. J. J. Am. Chem. Soc. 1983, 105, 6629-6637.
17. 3OH, 10:1) afforded 4d (230 mg, 1.41 mmol, 70%) as a colorless solid.