Titanium-catalyzed iminohydrazination of alkynes

Journal of Organometallic Chemistry

Volumn 690, Issue 23, 2005, Pages 5066-5077

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

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Catalysis; Hydroamination; Hydrohydrazination; Iminoamination; Iminohydrazination; Titanium

Indexed keywords

CATALYSIS; CATALYSTS; COMPLEXATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROBABILITY DENSITY FUNCTION; TITANIUM; TITANIUM COMPOUNDS;

HYDROAMINATION; HYDROHYDRAZINATION; IMINOAMINATION; IMINOHYDRAZINATION;

ORGANOMETALLICS;

EID: 27644499585     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.03.025     Document Type: Article

References (70)

1. For some reviews on multicomponent coupling reactions see I. Ugi, B. Werner, and A. Dömling Molecules 8 2003 53
2. A. Dömling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3168
3. I. Ugi, A. Dömling, and B. Werner J. Heterocyclic Chem. 37 2000 647
4. R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, and T.A. Keating Acc. Chem. Res. 29 1996 123
5. H. Bienaymé, C. Hulme, G. Oddon, and P. Schmitt Chem. Eur. J. 6 2000 3321
6. For some examples of recent transition metal-catalyzed multi-component coupling reactions see H.P. Hratchian, S.K. Chowdhury, V.M. Gutiérrez- Garcia, K.K.D. Amarasinhe, M.J. Heeg, H.G. Schlegel, and J. Montgomery Organometallics 23 2004 4636
7. R. Dhawan, R.D. Dghaym, and B.A. Arndtsen J. Am. Chem. Soc. 125 2003 1474
8. R. Dhawan, and B.A. Arndtsen J. Am. Chem. Soc. 126 2004 468
9. C. Cao, Y. Shi, and A.L. Odom J. Am. Chem. Soc. 125 2003 2880
10. For examples of hydrohydrazination catalyzed by late metals see J. Waser, and E.M. Carreira Angew. Chem., Int. Ed. 43 2004 4099
11. J. Waser, and E.M. Carreira J. Am. Chem. Soc. 126 2004 5676
12. C. Cao, Y. Shi, and A.L. Odom Org. Lett. 4 2002 2853
13. Y. Li, and A.L. Odom J. Am. Chem. Soc. 126 2004 1794
14. L. Ackermann, and R. Born Tetrahedron Lett. 45 2004 9541
15. V. Khedkar, A. Tillack, M. Michalik, and M. Beller Tetrahedron Lett. 45 2004 3123
16. For example see S.I. Yakimovich, I.V. Zerova, and T.E. Gabis J. Org. Chem. USSR 26 1990 2174
17. W.D. Jones, R.A. Schnettler, and E.W. Huber J. Heterocyclic Chem. 27 1990 511
18. D. Enders, V.N. Pathak, and P. Weuster Chem. Ber. 125 1992 515
19. These ligands have been put on most of the transition series. For recent examples of titanium nacnac chemistry see F. Basuli, J.C. Huffman, and D.J. Mindiola Inorg. Chem. 42 2003 8003
20. F. Basuli, L.A. Watson, J.C.H. Man, and D.J. Mindiola Dalton Trans. 2003 4228
21. F. Basuli, J. Tomaszewski, J.C. Huffman, and D.J. Mindiola J. Am. Chem. Soc. 125 2003 10170
22. F. Basuli, B.C. Bailey, J.C. Huffman, and D.J. Mindiola Chem. Commun. 2003 1554
23. F. Basuli, B.C. Bailey, J. Tomaszewski, J.C. Huffman, and D.J. Mindiola J. Am. Chem. Soc. 125 2003 6052
24. For a recent iron example see J. Vela, S. Vaddadi, T.R. Cundari, J.M. Smith, E.A. Gregory, R.J. Lachicotte, C.J. Flaschenriem, and P.L. Holland Organometallics 23 2004 5226
25. 3 (bap) (3) has only one of the donor amines coordinated in the solid-state, the bap ligand does have both amines coordinated in other structures we have collected. Y. Li, A.L. Odom, unpublished results.
26. A.M. Baranger, P.J. Walsh, and R.G. Bergman J. Am. Chem. Soc. 115 1993 2753
27. P.J. Walsh, A.M. Baranger, and R.G. Bergman J. Am. Chem. Soc. 114 1992 1708
28. A.P. Duncan, and R.G. Bergman Chem. Record 2 2002 431
29. S.Y. Lee, and R.G. Bergman Tetrahedron 51 1995 4255
30. For a review on related hydroamination see T.E. Müller, and M. Beller Chem. Rev. 98 1998 675
31. For some recent examples of intermolecular titanium-catalyzed hydroamination see T.-G. Ong, G.P.A. Yap, and D.S. Richeson Organometallics 21 2002 2839
32. J.M. Hoover, J.R. Petersen, J.H. Pikul, and A.R. Johnson Organometallics 23 2004 4614
33. V. Khedkar, A. Tillack, and M. Beller Org. Lett. 5 2003 4767
34. C. Lorber, R. Choukroun, and L. Vendier Organometallics 23 2004 1845
35. Z. Zhang, and L.L. Schaffer Org. Lett. 5 2003 4733
36. F. Pohlki, I. Bytschkov, H. Siebeneicher, A. Heutling, W.A. König, and S. Doye Eur. J. Org. Chem. 2004 1967
37. J.S. Johnson, and R.G. Bergman J. Am. Chem. Soc. 123 2001 2923
38. A. Tillack, I.G. Castro, C.G. Hartung, and M. Beller Angew. Chem., Int. Ed. 41 2002 2541
39. L. Ackermann Organometallics 22 2003 4367
40. I.G. Castro, A. Tillack, C.G. Hartung, and M. Beller Tetrahedron Lett. 44 2003 3217
41. A. Heutling, F. Pohlki, and S. Doye Chem. Eur. J. 10 2004 3059
42. C. Cao, Y. Li, Y. Shi, and A.L. Odom Chem. Commun. 2004 2002
43. Y. Shi, C. Hall, J.T. Ciszewski, C. Cao, and A.L. Odom Chem. Commun. 2003 586
44. B. Ramanathan, A.J. Keith, D. Armstrong, and A.L. Odom Org. Lett. 6 2004 2957
45. For an example of an isolable azatitanacyclobutene see B.D. Ward, A. Maisse-Francois, P. Mountford, and L.H. Gade Chem. Commun. 2004 704
46. S.I. Yakimovich, I.V. Zerova, and T.E. Gabis J. Org. Chem. USSR 26 1991 2174
47. Insertion of an alkyne into a transition metal-nitrogen bond is a rare but known reaction. For examples see N.A. Eckert, J.M. Smith, R.J. Lachicotte, and P.L. Holland Inorg. Chem. 43 2004 3306
48. E. Katayev, Y. Li, and A.L. Odom Chem. Commun. 2002 838 and references therein
49. P.D. Knight, I. Munslow, P.N. O'Shaughnessy, and P. Scott Chem. Commun. 2004 894
50. L. Ackermann, L.T. Kaspar, and C.J. Gschrei Org. Lett. 6 2004 2515
51. For mechanistic discussions see S. Hong, A.M. Kawaoka, and T.J. Marks J. Am. Chem. Soc. 125 2003 15878 and references therein
52. For a recent review of Ln-catalyzed hydroamination see S. Hong, and T.J. Marks Acc. Chem. Res. 37 2004 673
53. For recent examples of Group-3 and lanthanide catalyzed hydroamination reactions see M.R. Bürgstein, H. Berberich, and P.W. Roesky Organometallics 17 1998 1452
54. K.C. Hultzsch, F. Hampel, and T. Wagner Organometallics 23 2004 2601
55. G.A. Molander, and E.D. Dowdy J. Org. Chem. 64 1999 6515
56. Y.K. Kim, T. Livinghouse, and J.E. Bercaw Tetrahedron Lett. 42 2001 2933
57. Y.K. Kim, and T. Livinghouse Angew. Chem., Int. Ed. 41 2002 3645
58. Y. Li, and T.J. Marks J. Am. Chem. Soc. 120 1998 1757
59. D.V. Gribkov, and K.C. Hultzsch Chem. Commun. 2004 730
60. F. Lauterwasser, P.G. Hayes, S. Bräse, W.E. Piers, and L.L. Schafer Organometallics 23 2004 2234
61. E. Benzing, and W. Kornicker Chem. Ber. 94 1961 2263
62. The hydrazido(2-) mono(dap) complex suggested in Scheme 4 has recently been prepared and appears to be on the catalytic cycle. It is currently being more fully characterized and is under scrutiny in our laboratory.
63. A. Tillack, H. Jiao, I.G. Castro, C.G. Hartung, and M. Beller Chem. Eur. J. 10 2004 2409
64. D.C. Bradley, and I.M. Thomas J. Chem. Soc. 1960 3859
65. W. Herz, and K. Dittmer J. Am. Chem. Soc. 69 1947 1698
66. H. Kim, and R.L. Elsenbaumer Tetrahedron Lett. 39 1998 1087
67. G.W. Gokel, R.P. Widera, and W.P. Weber Org. Synth. 55 1979 96
68. H.M. Walborsky, and G.E. Niznik J. Org. Chem. 37 1972 187
69. A.D. Becke J. Chem. Phys. 98 1993 1372
70. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision C.02 2004 Gaussian, Inc. Wallingford, CT