A Dramatic Effect of Aryloxo Ligands on the Titanium-Catalyzed Hydroamination of Alkynes

Organic Letters

Volumn 5, Issue 25, 2003, Pages 4767-4770

  Khedkar, Vivek ^a   Tillack, Annegret ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC AMINE; ALKYNE DERIVATIVE; AROMATIC AMINE; IMINE; LIGAND; TITANIUM; TITANIUM DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; HYDROAMINATION; METHODOLOGY;

EID: 0346337194     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035653+     Document Type: Article

References (52)

1. Recent reviews: (a) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104. (b) Nobis, M.; Driessen-Hölscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983. (c) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
2. Recent reviews: (a) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104. (b) Nobis, M.; Driessen-Hölscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983. (c) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
3. Recent reviews: (a) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104. (b) Nobis, M.; Driessen-Hölscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983. (c) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
4. (a) Garcia Castro, I.; Tillack, A.; Hartung, C. G.; Beller, M. Tetrahedron Lett. 2003, 44, 3217.
5. (b) Haak, E.; Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2002, 457.
6. (c) Siebeneicher, H.; Doye, S. Eur. J. Org. Chem. 2002, 1213.
7. (a) Barluenga, J.; Aznar, A.; Liz, R.; Rodes, R. J. Chem. Soc., Perkin Trans. 1 1980, 2732.
8. (b) Barluenga, J.; Aznar, A. Synthesis 1977, 195.
9. (c) Barluenga, J.; Aznar, A. Synthesis 1975, 704.
10. (a) Tzalis, D.; Koradin, C.; Knochel, P. Tetrahedron Lett. 1999, 40, 6193.
11. (a) Li, C.; Thomson, R. K.; Gillon, B.; Patrick, B. O.; Schafer, L. L. Chem. Commun. 2003, 2462.
12. (b) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935.
13. (c) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961.
14. (d) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799.
15. (e) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923.
16. (f) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2001, 4411.
17. (g) Haak, E.; Siebeneicher, H.; Doye, S. Org. Lett. 2000, 2, 1935.
18. (h) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389.
19. (i) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753.
20. (j) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708.
21. (a) Mizushima, E.; Hayashi, T.; Tanaka, M. Org. Lett. 2003, 5, 3349.
22. (b) Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12670.
23. (c) Hartung, C. G.; Tillack, A.; Trauthwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339.
24. (d) Tokunaga, M.; Wakatsuki, Y. J. Synth. Org. Chem. Jpn. 2000, 58, 587.
25. (e) Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1999, 38, 3222.
26. (f) Uchimaru, Y. Chem. Commun. 1999, 1133.
27. (g) Kadota, I.; Shibuya, A.; Lutete, L. M.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4570.
28. (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757.
29. (b) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770.
30. (a) Wang, J.; Dash, A. K.; Kapon, M.; Berthet, J.-C.; Ephritikhine, M.; Eisen, M. S. Chem. Eur. J. 2002, 8, 5384.
31. (b) Straub, T.; Haskel, A.; Neyround, T. G.; Kapon, M.; Botoshansky, M.; Eisen, M. S. Organometallics 2001, 20, 5017.
32. (c) Eisen, M. S.; Straub, T.; Haskel, A. J. Alloys Compd. 1998, 271-273, 116.
33. (d) Haskel, A.; Straub, T.; Eisen, M. S. Organometallics 1996, 15, 3773.
34. (a) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. See also ref 5 (e, i, j).
35. (a) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305. See also ref 5 (b-d, f-h).
36. (a) Tillack, A.; Garcia Castro, I.; Hartung, C. G.; Beller, M. Angew. Chem., Int. Ed. 2002, 41, 2541.
37. Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967.
38. (a) Shi, Y.; Hall, C.; Ciszewski, J. T.; Cao, C.; Odom, A. L. Chem. Commun. 2003, 584.
39. (b) Cao, C.; Shi, Y. H.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880.
40. (c) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853.
41. (d) Cao, C.; Ciszewski, T.; Odom, A. L. Organometallics 2001, 20, 5011.
42. Ong, T. G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839.
43. Selected recent examples: (a) Himes, R. A.; Fanwick, P. E.; Rothwell, I. P. Chem. Commun. 2003, 18. (b) Gonzalez-Maupoey, M.; Cuenca, T.; Frutos, L. M.; Castano, O.; Herdtweck, E. Organometallics 2003, 22, 2694. (c) Sturla, S. J.; Buchwald, S. L. Organometallics 2002, 21, 739. (d) Michalczyk, L.; de Gala, S.; Bruno, J. W. Organometallics 2001, 20, 5547. (e) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. (f) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223. (g) Thorn, M. G.; Etheridge, Z. C.; Fanwick, P. E.; Rothwell, I. P. J. Organomet. Chem. 1999, 591, 148. (h) Waratuke, S. A.; Thorn, M. G.; Fanwick, P. E.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1999, 121, 9111.
44. Selected recent examples: (a) Himes, R. A.; Fanwick, P. E.; Rothwell, I. P. Chem. Commun. 2003, 18. (b) Gonzalez-Maupoey, M.; Cuenca, T.; Frutos, L. M.; Castano, O.; Herdtweck, E. Organometallics 2003, 22, 2694. (c) Sturla, S. J.; Buchwald, S. L. Organometallics 2002, 21, 739. (d) Michalczyk, L.; de Gala, S.; Bruno, J. W. Organometallics 2001, 20, 5547. (e) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. (f) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223. (g) Thorn, M. G.; Etheridge, Z. C.; Fanwick, P. E.; Rothwell, I. P. J. Organomet. Chem. 1999, 591, 148. (h) Waratuke, S. A.; Thorn, M. G.; Fanwick, P. E.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1999, 121, 9111.
45. Selected recent examples: (a) Himes, R. A.; Fanwick, P. E.; Rothwell, I. P. Chem. Commun. 2003, 18. (b) Gonzalez-Maupoey, M.; Cuenca, T.; Frutos, L. M.; Castano, O.; Herdtweck, E. Organometallics 2003, 22, 2694. (c) Sturla, S. J.; Buchwald, S. L. Organometallics 2002, 21, 739. (d) Michalczyk, L.; de Gala, S.; Bruno, J. W. Organometallics 2001, 20, 5547. (e) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. (f) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223. (g) Thorn, M. G.; Etheridge, Z. C.; Fanwick, P. E.; Rothwell, I. P. J. Organomet. Chem. 1999, 591, 148. (h) Waratuke, S. A.; Thorn, M. G.; Fanwick, P. E.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1999, 121, 9111.
46. Selected recent examples: (a) Himes, R. A.; Fanwick, P. E.; Rothwell, I. P. Chem. Commun. 2003, 18. (b) Gonzalez-Maupoey, M.; Cuenca, T.; Frutos, L. M.; Castano, O.; Herdtweck, E. Organometallics 2003, 22, 2694. (c) Sturla, S. J.; Buchwald, S. L. Organometallics 2002, 21, 739. (d) Michalczyk, L.; de Gala, S.; Bruno, J. W. Organometallics 2001, 20, 5547. (e) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. (f) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223. (g) Thorn, M. G.; Etheridge, Z. C.; Fanwick, P. E.; Rothwell, I. P. J. Organomet. Chem. 1999, 591, 148. (h) Waratuke, S. A.; Thorn, M. G.; Fanwick, P. E.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1999, 121, 9111.
47. Selected recent examples: (a) Himes, R. A.; Fanwick, P. E.; Rothwell, I. P. Chem. Commun. 2003, 18. (b) Gonzalez-Maupoey, M.; Cuenca, T.; Frutos, L. M.; Castano, O.; Herdtweck, E. Organometallics 2003, 22, 2694. (c) Sturla, S. J.; Buchwald, S. L. Organometallics 2002, 21, 739. (d) Michalczyk, L.; de Gala, S.; Bruno, J. W. Organometallics 2001, 20, 5547. (e) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. (f) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223. (g) Thorn, M. G.; Etheridge, Z. C.; Fanwick, P. E.; Rothwell, I. P. J. Organomet. Chem. 1999, 591, 148. (h) Waratuke, S. A.; Thorn, M. G.; Fanwick, P. E.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1999, 121, 9111.
48. Selected recent examples: (a) Himes, R. A.; Fanwick, P. E.; Rothwell, I. P. Chem. Commun. 2003, 18. (b) Gonzalez-Maupoey, M.; Cuenca, T.; Frutos, L. M.; Castano, O.; Herdtweck, E. Organometallics 2003, 22, 2694. (c) Sturla, S. J.; Buchwald, S. L. Organometallics 2002, 21, 739. (d) Michalczyk, L.; de Gala, S.; Bruno, J. W. Organometallics 2001, 20, 5547. (e) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. (f) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223. (g) Thorn, M. G.; Etheridge, Z. C.; Fanwick, P. E.; Rothwell, I. P. J. Organomet. Chem. 1999, 591, 148. (h) Waratuke, S. A.; Thorn, M. G.; Fanwick, P. E.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1999, 121, 9111.
49. Selected recent examples: (a) Himes, R. A.; Fanwick, P. E.; Rothwell, I. P. Chem. Commun. 2003, 18. (b) Gonzalez-Maupoey, M.; Cuenca, T.; Frutos, L. M.; Castano, O.; Herdtweck, E. Organometallics 2003, 22, 2694. (c) Sturla, S. J.; Buchwald, S. L. Organometallics 2002, 21, 739. (d) Michalczyk, L.; de Gala, S.; Bruno, J. W. Organometallics 2001, 20, 5547. (e) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. (f) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223. (g) Thorn, M. G.; Etheridge, Z. C.; Fanwick, P. E.; Rothwell, I. P. J. Organomet. Chem. 1999, 591, 148. (h) Waratuke, S. A.; Thorn, M. G.; Fanwick, P. E.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1999, 121, 9111.
50. Selected recent examples: (a) Himes, R. A.; Fanwick, P. E.; Rothwell, I. P. Chem. Commun. 2003, 18. (b) Gonzalez-Maupoey, M.; Cuenca, T.; Frutos, L. M.; Castano, O.; Herdtweck, E. Organometallics 2003, 22, 2694. (c) Sturla, S. J.; Buchwald, S. L. Organometallics 2002, 21, 739. (d) Michalczyk, L.; de Gala, S.; Bruno, J. W. Organometallics 2001, 20, 5547. (e) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. (f) Okamoto, S.; Livinghouse, T. J. Am. Chem. Soc. 2000, 122, 1223. (g) Thorn, M. G.; Etheridge, Z. C.; Fanwick, P. E.; Rothwell, I. P. J. Organomet. Chem. 1999, 591, 148. (h) Waratuke, S. A.; Thorn, M. G.; Fanwick, P. E.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1999, 121, 9111.
51. Rothwell and co-worker reported the synthesis of an aryloxo(imido)- titanium complex and the hydroamination of the internal alkyne 3-hexyne: Hill, J. E.; Profilet, R. D.; Fanwick, P. E.; Rothwell, I. P. Angew. Chem., Int. Ed. Engl. 1990, 29, 664.
52. Duff, A. W.; Kamarudin, R. A.; Lappert, M. F.; Norton, R. J. J. Chem. Soc., Dalton Trans. 1986, 489.