Intermolecular alkyne hydroaminations involving 1,1-disubstituted hydrazines

Organic Letters

Volumn 4, Issue 17, 2002, Pages 2853-2856

  Cao, Changsheng ^a   Shi, Yanhui ^a   Odom, Aaron L ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; HYDRAZINE DERIVATIVE; INDOLE DERIVATIVE; TITANIUM;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; CATALYSIS; CYCLIZATION; HYDRAZINES; INDOLES; TITANIUM;

EID: 0000931907     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0201052     Document Type: Article

References (54)

1. Reviews relevant to hydroamination: (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
2. (b) Roundhill, D. M. Chem. Rev. 1992, 92, 1.
3. (c) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163.
4. Leading examples of intermolecular hydroamination of alkenes: (a) Hartung, C. G.; Breindl, C.; Tillack, A.; Beller, M. Tetrahedron 2000, 56, 5157-5162.
5. (b) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546-9547.
6. (c) Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Müller, T. E. Eur. J. Inorg. Chem. 1999, 1121-1132.
7. (d) Trauthwein, H.; Tillack, A.; Beller, M. Chem. Commun. 1999, 2029-2030.
8. (e) Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Herwig, J.; Müller, T. E.; Thiel, O. R. Chem. Eur. J. 1999, 5, 1306-1319.
9. (f) Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Müller, T. E.; Zapf, A. J. Organomet. Chem. 1998, 566, 277-286.
10. (g) Beller, M.; Eichberger, M.; Trauthwein, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 2225-2226.
11. Hartung, C. G.; Tillack, A.; Trauthwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339-6343.
12. (a) Kadota, I.; Shibuya, A.; Lutete, L. M.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4570-4571.
13. (b) Yamamoto, Y.; Radhakrishnan, U. Chem. Soc. Rev. 1999, 28, 199-207.
14. Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1999, 38, 3222-3225.
15. (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757-1771.
16. (b) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770-3772.
17. (a) Straub, T.; Haskel, A.; Neyroud, T. G.; Kapon, M.; Botoshansky, M.; Eisen, M. S. Organometallics 2001, 20, 5017-5035.
18. (b) Haskel, A.; Straub, T.; Eisen, M. S. Organometallics 1996, 15, 3773-3775.
19. (c) Straub, T.; Frank, W.; Reiss, G. J.; Eisen, M. S. J. Chem. Soc., Dalton Trans. 1996, 2541-2546.
20. (a) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305-2308.
21. (b) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923-2924.
22. (c) Siebeneicher, H.; Doye, S. J. Prakt. Chem. Chem. Ztg. 2000, 341, 102-106.
23. (d) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389-3391.
24. (e) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2001, 4411-4418.
25. (f) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967-3969.
26. (g) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011-5013.
27. Seminal mechanistic studies on Group IV metal-catalyzed hydroamination: (a) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632-4635.
28. (b) Sweeney, Z. K.; Salsman, J. L.; Anderson, R. A.; Bergman, R. G. Angew. Chem., Int. Ed. 2000, 39, 2339-2343.
29. (c) Polse, J. L.; Anderson, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 13405-13414.
30. (d) Baranger, A, M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763.
31. (e) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719.
32. Some electron-deficient alkynes react directly with hydrazines. (a) Hamper, B. C.; Kurtzweil, M. L.; Beck, J. P. J. Org. Chem. 1992, 57, 5680-5686.
33. (b) Tolchinskii, S. E.; Marentina, I. A.; Petrov, A. A. J. Org. Chem. USSR 1980, 16, 992-998.
34. For some related transformations, see: (a) Barluenga, J.; Aznar, F.; Liz, R.; Bayod, M. Chem. Commun. 1988, 121-122.
35. (b) Kauffmann, Th. Angew. Chem., Int. Ed. Engl. 1964, 3, 342-361.
36. (c) For the related hydroamination of allene by 1,1-dimethylhydrazine, see ref 8b.
37. In the titanium dpma system, electronic effects of terminal hydrazido(2-) functional groups and bridging hydrazido(2-) ligands, potential intermediates in the hydroamination catalytic cycle, have been isolated and studied. Li, Y.; Odom, A. L., unpublished results.
38. Harris, S. A.; Ciszewski, J. T.; Odom, A. L. Inorg. Chem. 2001, 40, 1987-1988. dpma is N,N-di(pyrrolyl-α-methyl)-N-methylamine.
39. (a) Herz, W.; Dittmer, K.; J. Am. Chem. Soc. 1947, 69, 1698-1700.
40. (b) Kim, H.; Elsenbaumer, R. L. Tetrahedron Lett. 1998, 39, 1087.
41. Group IV dap complexes: (a) Huang, J. H.; Chi, L.-S.; Huang, F.-M.; Kuo, P.-C.; Peng, S.-M. J. Chin. Chem. Soc. 2000, 47, 895-900.
42. (b) Huang, J. H.; Kuo, P.-C.; Lee, G. H.; Peng, S.-M. J. Chin. Chem. Soc. 2000, 47, 1191-1195.
43. (c) Drevs, H.; Schmeiber, A.; Hartung, H.; Baumeister, U. Chem. Ber. 1996, 129, 853-857.
44. 1-hydrazido(2-) electronics, see: Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds; Wiley & Sons: New York, 1988.
45. 2 because the bis[μ-hydrazido(2-)] compound is formed irreversibly under the reaction conditions (ref 12).
46. See ref 9d for a discussion of electronic effects in Group IV metal-catalyzed hydroamination.
47. Preparation of hydrazines that are not commercially available was accomplished using literature procedures, (a) 1-Aminoindolene and 1-amino-2,3,4-tetrahydroquinoline: Kost, A. N.; Yudin, L. G.; Berlin, Y. A.; Terent'ev, A. P. Zh. Obshch. Khim. 1959, 29, 3820.
48. (b) 1-Aminoindole and 1-amino-3-methylindole: Somei, M.; Matsubara, M.; Kanda, Y.; Natsume, M. Chem. Pharm. Bull. 1978, 26, 2522-2534. All other hydrazines were purchased from commercial sources and distilled prior to use.
49. (a) Robinson, B. The Fischer Indole Synthesis; Wiley & Sons: Chichester, UK, 1982.
50. (b) Recent review of indole syntheses: Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045-1075.
51. Hydroamination, usually intramolecular, previously has been used for the generation of indoles. (a) Kondo, T.; Okada, T.; Suzuki, T.; Mitsudo, T. J. Organomet. Chem. 2001, 622, 149-154.
52. (b) Beller, M.; Thiel, O. R.; Trauthwein, H.; Hartung, C. G. Chem. Eur. J. 2000, 6, 2513-2522.
53. (c) Burling, S.; Field, L. D.; Messerle, B. A. Organometallics 2000, 19, 87-90.
54. (d) Tokunaga, M.; Ota, M.; Haga, M.; Wakatsuki, Y. Tetrahedron Lett. 2001, 42, 3865-3868.