Regioselective preparation of 2-phenylethylamines from 1-phenyl-2-alkyl- alkynes by hydroamination/reduction sequences

Synthesis

Volumn , Issue 7, 2005, Pages 1200-1204

  Heutling, Andreas ^a   Severin, René ^a   Doye, Sven ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkynes; Aminations; Amines; Catalysis; Titanium

Indexed keywords

CATALYSTS; HYDROCARBONS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ALKYNES; HYDROAMINATION; PHENYLETHYLAMINES;

AMINES;

ALIPHATIC AMINE; ALKYL GROUP; ALKYNE DERIVATIVE; IMINE; PHENETHYLAMINE DERIVATIVE; PHENYL GROUP; ZINC;

AMINATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECOMPOSITION; HYDROAMINATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; REPRODUCIBILITY; ROOM TEMPERATURE; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; TECHNIQUE;

EID: 18744362215     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834863     Document Type: Article

References (42)

1. Reviews: (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
2. (b) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104.
3. (c) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079.
4. Review: Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935.
5. (a) Siebeneicher, H.; Doye, S. Eur. J. Org. Chem. 2002, 1213.
6. (b) Bytschkov, I.; Siebeneicher, H.; Doye, S. Eur. J. Org. Chem. 2003, 2888.
7. (a) Doye, S.; Haak, E. German Patent DE 19913522, 2000; Chem. Abstr. 2000, 133, 266588.
8. (b) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem. Int. Ed. 1999, 38, 3389;
9. Angew. Chem. 1999, 111, 3584.
10. (c) Bytschkov, I.; Doye, S. Tetrahedron Lett. 2002, 43, 3715.
11. (d) For early studies on Ti-catalyzed intramolecular hydroaminations of alkynes, see: McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459.
12. (e) See also: McGrane, P. L.; Livinghouse, T. J. Org. Chem. 1992, 57, 1323.
13. (f) See also: McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485.
14. (a) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961.
15. (b) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799.
16. (a) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923.
17. (b) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475.
18. (c) Ackermann, L.; Bergman, R. G.; Loy, R. N. J. Am. Chem. Soc. 2003, 125, 11956.
19. (a) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967.
20. (b) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011.
21. (c) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853.
22. (d) Shi, Y.; Hall, C.; Ciszewski, J. T.; Cao, C.; Odom, A. L. Chem. Commun. 2003, 586.
23. (e) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880.
24. (f) Li, Y.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2004, 126, 1794.
25. (a) Tillack, A.; Garcia Castro, I.; Hartung, C. G.; Beller, M. Angew. Chem. Int. Ed. 2002, 41, 2541;
26. Angew. Chem. 2002, 114, 2646.
27. (b) Garcia Castro, I.; Tillack, A.; Hartung, C. G.; Beller, M. Tetrahedron Lett. 2003, 44, 3217.
28. (c) Khedkar, V.; Tillack, A.; Beller, M. Org. Lett. 2003, 5, 4767.
29. (d) Khedkar, V.; Tillack, A.; Michalik, M.; Beller, M. Tetrahedron Lett. 2004, 45, 3123.
30. (e) Tillack, A.; Jiao, H.; Garcia Castro, I.; Hartung, C. G.; Beller, M. Chem. Eur. J. 2004, 10, 2409.
31. (a) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839.
32. (b) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. J. Am. Chem. Soc. 2003, 125, 8100.
33. (a) Li, C.; Thomson, R. K.; Gillon, B.; Patrick, B. O.; Schafer, L. L. Chem. Commun. 2003, 2462.
34. (b) Zhang, Z.; Schafer, L. L. Org. Lett. 2003, 5, 4733.
35. Ackermann, L. Organometallics 2003, 22, 4367.
36. Lorber, C.; Choukroun, R.; Vendier, L. Organometallics 2004, 25, 1845.
37. Ward, B. D.; Maisse-Francois, A.; Mountford, P.; Gade, L. H. Chem. Commun. 2004, 704.
38. Heutling, A.; Pohlki, F.; Doye, S. Chem. Eur. J. 2004, 10, 3059.
39. Balboni, D.; Camurati, I.; Prini, G.; Resconi, L.; Galli, S.; Mercandelli, P.; Sironi, A. Inorg. Chem. 2001, 40, 6588; and references cited therein.
40. www.mcat.de.
41. Lüllmann, H.; Mohr, K.; Ziedler, K. Taschenatlas der Pharmakologie, 3rd ed.; Thieme: Stuttgart, 1996, 80.
42. Kim, S.; Oh, C. H.; Ko, J. S.; Ahn, K. H.; Kim, Y. J. J. Org. Chem. 1985, 50, 1927.