Microwave-assisted catalytic intermolecular hydroamination of alkynes

European Journal of Organic Chemistry

Volumn , Issue 23, 2001, Pages 4411-4418

  Bytschkov, Igor ^a   Doye, Sven ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

Alkynes; Aminations; Homogeneous catalysis; Microwave irradiation; Titanium

Indexed keywords

ALKYNE DERIVATIVE; DIMETHYLTITANOCENE; TITANOCENE; TOLUENE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYST; IRRADIATION; MICROWAVE RADIATION; STEREOCHEMISTRY; TECHNOLOGY;

EID: 0035208215     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200112)2001:23<4411::aid-ejoc4411>3.0.co;2-n     Document Type: Article

References (54)

1. For general reviews, see: [1a] I. A. Chekulaeva, L. V. Kondratjeva, Russ. Chem. Rev. 1965, 34, 669-680;
2. [1b] R. Taube in Applied Homogeneous Catalysis with Organometallic Compounds (Eds.: B. Cornils, W. A. Herrmann), VCH-Verlagseesellschaft, Weinheim, 1996, p. 507-520;
3. [1c] T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675-703;
4. [1d] T. E. Müller, M. Beller in Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998, vol. 2, p. 316-330;
5. [1e] E. Haak, S. Doye, Chem. Unserer Zeit 1999, 33, 296-303.
6. For catalytic intramolecular hydroamination of aminoalkynes, see: [2a] K. Utimoto, Pure Appl. Chem. 1983, 55, 1845-1852;
7. [2b] Y. Fukuda, K. Utimoto, H. Nozaki, Heterocycles 1987, 25, 297-300;
8. [2c] P. L. McGrane, M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1992, 114, 5459-5460;
9. [2d] P. L. McGrane, T. Livinghouse, J. Org. Chem. 1992, 57, 1323-1324;
10. [2e] P. L. McGrane, T. Livinghouse, J. Am. Chem. Soc. 1993, 115, 11485-11489;
11. [2f] D. Fairfax, M. Stein, T. Livinghouse, M. Jensen, Organometallics 1997, 16, 1523-1525;
12. [2g] Y. Li, P.-F. Fu, T. J. Marks, Organometallics 1994, 13, 439-440;
13. [2h] Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 9295-9306;
14. [2i] Y. Li, T. J. Marks, J. Am. Chem. Soc. 1998, 120, 1757-1771;
15. [2j] E. M. Campi, W. R. Jackson, J. Organomet. Chem. 1996, 523, 205-209;
16. [2k] M. R. Bürgstein, H. Berberich, P. W. Roesky, Organometallics 1998, 17, 1452-1454;
17. [2l] T. E. Müller, Tetrahedron Lett. 1998, 39, 5961-5962;
18. [2m] T. E. Müller, M. Grosche, E. Herdtweck, A.-K. Pleier, E. Walter, Y.-K. Yan, Organometallics 2000, 19, 170-183;
19. [2n] S. Burling, L. D. Fields, B. A. Messerle, Organometallics 2000, 19, 87-90;
20. [2o] Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933-2935;
21. [2p] T. Kondo, T. Okada, T. Suzuki, T.-a. Mitsudo, J. Organomet. Chem. 2001, 622, 149-154.
22. For catalytic intermolecular hydroamination of alkynes, see: [3a] J. Barluenga, F. Aznar, Synthesis 1977, 195-198;
23. [3b] J. Barluenga, F. Aznar, R. Liz, R. Rodes, J. Chem. Soc., Perkin Trans. 1 1980, 2732-2737;
24. [3c] P. J. Walsh, A. M. Baranger, R. G. Bergman, J. Am. Chem. Soc. 1992, 114, 1708-1719;
25. [3d] A. M. Baranger, P. J. Walsh, R. G. Bergman, J. Am. Chem. Soc. 1993, 115, 2753-2763;
26. [3e] Y. Li, T. J. Marks, Organometallics 1996, 15, 3770-3772;
27. [3f] A. Haskel, T. Straub, M. S. Eisen, Organometallics 1996, 15, 3773-3775;
28. [3g] M. Tokunaga, M. Eckert, Y. Wakatsuki, Angew. Chem. 1999, 111, 3416-3419;
29. Angew. Chem. Int. Ed. 1999, 38, 3222-3225;
30. [3h] D. Tzalis, C. Koradin, P. Knochel, Tetrahedron Lett. 1999, 40, 6193-6195;
31. [2g,5]
32. [4a] N. A. Petasis in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), John Wiley & Sons, 1995, vol. 1, p. 470-473, and references therein;
33. [4b] H. Siebeneicher, S. Doye, J. Prakt. Chem. 2000, 342, 102-106.
34. [5a] E. Haak, I. Bytschkov, S. Doye, Angew. Chem. 1999, 111, 3584-3586;
35. Angew. Chem. Int. Ed. 1999, 38, 3389-3391;
36. [5b] E. Haak, H. Siebeneicher, S. Doye, Org. Lett. 2000, 2, 1935-1937;
37. [5c] F. Pohlki, S. Doye, Angew. Chem. 2001, 113, 2361-2364;
38. Angew. Chem. Int. Ed. 2001, 40, 2305-2308.
39. For a critical review of the application of microwaves in organic chemistry, see: J. Herwig, R. Trainor in Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998, vol. 2, p. 436-441, and references therein.
40. Since all reactions were performed in sealed Schlenk tubes, it was not possible to determine the temperature inside the reaction mixtures during the microwave experiments.
41. For example, see: P. Bravo, M. Guidetti, F. Viani, M. Zanda, A. L. Markovsky, A. E. Sorochinsky, I. V. Soloshonok, V. A. Soloshonok, Tetrahedron 1998, 54, 12789-12806.
42. T. Ikariya, Y. Ishikawa, K. Hirai, S. Yoshikawa, J. Organomet. Chem. 1985, 288, 311-315.
43. K. Mori, H. Sugiyama, M. Sekiya, Chem. Pharm. Bull. 1971, 19, 1722-1727.
44. M. Montagne, G. Rousseau, C. R. Hebd. Seances Acad. Sci. 1933, 196, 1165-1167.
45. U. B. Paulsen-Sörman, K.-H. Jönsson, B. G. A. Lindeke, J. Med. Chem. 1984, 27, 342-346.
46. R. W. Franck, Sr., J. M. Gilligan, J. Org. Chem. 1971, 36, 222-224.
47. R. S. Varma, R. Dahiya, Tetrahedron 1998, 54, 6293-6298.
48. J. A. Marshall, J. Lebreton, J. Am. Chem. Soc. 1988, 110, 2925-2931.
49. M. Takamatsu, M. Sekiya, Chem. Pharm. Bull. 1981, 29, 616-622.
50. I. Lee, W. H. Lee, H. W. Lee, T. W. Bentley, J. Chem. Soc., Perkin Trans. 2 1993, 141-146.
51. T. V. Stupnikova, A. I. Serdyuk, V. N. Kalafat, R. S. Sagitullin, V. P. Marshtupa, Chem. Heterocycl. Compd. (Engl. Transl.) 1981, 367-369.
52. M. B. Gasc, J. Perie, A. Lattes, Tetrahedron 1978, 34, 1943-1950.
53. E. B. Glebova, T. N. Wischnjakova, Neftekhimia 1976, 16, 614-618.
54. F. Tanaka, J. Pharm. Soc. Jpn. 1943, 63, 343-353.