Hydroamination of Alkynes Catalyzed by Imido Complexes of Titanium and Vanadium

Organometallics

Volumn 23, Issue 8, 2004, Pages 1845-1850

  Lorber, Christian ^a   Choukroun, Robert ^a   Vendier, Laure ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSTS; COMPLEXATION; DIMERS; GAS CHROMATOGRAPHY; ISOMERS; OLIGOMERS; POLYMERIZATION; SUBSTRATES; VANADIUM; X RAYS;

HYDROAMINATION; IMIDO COMPLEXES; METAL COMPLEXES;

TITANIUM;

EID: 2342430645     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0342762     Document Type: Article

References (81)

1. Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
2. Trost, M. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
3. For recent reviews on alkyne hydroamination, see ref 1 and: (a) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104. (b) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935.
4. For recent reviews on alkyne hydroamination, see ref 1 and: (a) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104. (b) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935.
5. (a) Barluenga, J.; Aznar, F. Synthesis 1977, 195.
6. (b) Barluenga, J.; Aznar, F.; Liz, R.; Rodes, R. J. Chem. Soc., Perkin Trans. 1 1980, 2732.
7. Seayad, J.; Tillack, A.; Hartung, C. G. Beller, M. Adv. Synth. Catal. 2002, 344, 795.
8. (a) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770.
9. (b) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757.
10. (c) Ryu, J.-S.; Li, G. Y.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 12584.
11. (a) Straub, T.; Askel, A.; Neyroud, T. G.; Kapon, M.; Botoshansky, M.; Eisen, M. S. Organometallics 2001, 20, 5017.
12. (b) Askel, A.; Straub, T.; Eisen, M. S. Organometallics 1998, 15, 3773.
13. (a) Wartchow, R.; Doye, S. J. Organomet. Chem. 1998, 566, 287.
14. (b) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708.
15. (c) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753.
16. (d) Walsh, P. J.; Hollander, F. J.; Bergman, R. G. Organometallics 1993, 12, 3705.
17. (a) Uchimaru, Y. Chem. Commun. 1999, 1133.
18. (b) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1999, 38, 3222.
19. Hartung, C. G.; Tillack, A.; Trautwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339.
20. (a) Müller, T. E. Tetrahedron Lett. 1998, 39, 5961.
21. (b) Yamamoto, Y.; Radhakrishnan, U. Chem. Soc. Rev. 1999, 28, 199.
22. Mizushima, E.; Hayashi, T.; Tanaka, M. Org. Lett. 2003, 5, 3349.
23. (a) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389.
24. (b) Siebeneicher, H.; Doye, S. J. Prakt. Chem. 2000, 342, 102.
25. (c) Bytschkov, I.; Doye, S. Tetrahedron Lett. 2002, 43, 3715.
26. (d) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2001, 4411.
27. (e) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hottop, T.; Doye, S. Synlett 2002, 799.
28. (f) Siebeneicher, H.; Doye, S. Eur. J. Org. Chem. 2002, 1213.
29. (g) Heutling, A.; Doye, S. J. Org. Chem. 2002, 67, 1961.
30. (a) Tillack, A.; Castro, I. G.; Hartung, C. G.; Beller, M. Angew. Chem., Int. Ed. 2002, 41, 2541.
31. (b) Castro, I. G.; Tillack, A.; Hartung, C. G.; Beller, M. Tetrahedron 2003, 44, 3217.
32. (a) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839.
33. (b) Li, C.; Thomson, R. K.; Gillon, B.; Patrick, B. O.; Schafer, L. L. Chem. Commun. 2003, 2462.
34. (c) Hill, J. E.; Profilet, R. D.; Fanwick, P. E.; Rothwell, I. P. Angew. Chem., Int. Ed. Engl. 1990, 29, 664.
35. (d) Ackermann, L.; Bergman, R. G.; Loy, R. N. J. Am. Chem. Soc. 2003, 125, 11956.
36. (e) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475.
37. (a) Shi, Y.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 3967.
38. (b) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011.
39. (c) Shi, Y.; Hall, C.; Ciszewski, J. T.; Cao, C.; Odom, A. L. Chem. Commun. 2003, 586.
40. (d) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853.
41. For mechanistic considerations on group 4 metal-catalyzed alkyne hydroamination, see: (a) Lee, S. Y.; Bergman, R. G. Tetrahedron Lett. 1995, 51, 4255. (b) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (c) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (d) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305.
42. For mechanistic considerations on group 4 metal-catalyzed alkyne hydroamination, see: (a) Lee, S. Y.; Bergman, R. G. Tetrahedron Lett. 1995, 51, 4255. (b) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (c) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (d) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305.
43. For mechanistic considerations on group 4 metal-catalyzed alkyne hydroamination, see: (a) Lee, S. Y.; Bergman, R. G. Tetrahedron Lett. 1995, 51, 4255. (b) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (c) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (d) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305.
44. For mechanistic considerations on group 4 metal-catalyzed alkyne hydroamination, see: (a) Lee, S. Y.; Bergman, R. G. Tetrahedron Lett. 1995, 51, 4255. (b) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923. (c) Straub, B. F.; Bergman, R. G. Angew. Chem., Int. Ed. 2001, 40, 4632. (d) Pohlki, F.; Doye, S. Angew. Chem., Int. Ed. 2001, 40, 2305.
45. (a) Lorber, C.; Donnadieu, B.; Choukroun, R. Organometallics 2000, 19, 1963.
46. (b) Choukroun, R.; Wolff, F.; Lorber, C.; Donnadieu, B. Organometallics 2003, 22, 2245.
47. (c) Choukroun, R.; Lorber, C.; Lepetit, C.; Donnadieu, B. Organometallics 2003, 22, 1995.
48. (d) Douziech, B.; Choukroun, R.; Lorber, C.; Donnadieu, B. J. Organomet. Chem. 2002, 649, 15.
49. (a) Lorber, C.; Choukroun, R.; Donnadieu, B. Inorg. Chem. 2003, 42, 673.
50. (b) Lorber, C.; Choukroun, R.; Donnadieu, B. Inorg. Chem. 2002, 41, 4217.
51. (c) Choukroun, R.; Donnadieu, B.; Lorber, C.; Pellny, P.-M.; Baumann, W.; Rosenthal, U. Chem. Eur. J. 2000, 6, 4505.
52. (d) Choukroun, R.; Donnadieu, B.; Lorber, C. Chem. Eur. J. 2002, 8, 2700.
53. (e) Choukroun, R.; Lorber, C.; Donnadieu, B. Organometallics 2002, 21, 1124.
54. (f) Wolff, F.; Choukroun, R.; Lorber, C.; Donnadieu, B. Eur. J. Inorg. Chem. 2003, 628.
55. (g) Wolff, F.; Lorber, C.; Choukroun, R.; Donnadieu, B. Inorg. Chem. 2003, 42, 7839.
56. (h) Lorber, C.; Donnadieu, B.; Choukroun, R. J. Chem. Soc., Dalton Trans. 2000, 4497.
57. 4). However, with our vanadium catalysts, the effect of a larger excess of aniline is less important.
58. If we assume that an imido functionality is the key intermediate for vanadium-catalyzed alkyne hydroamination (as demonstrated with titanium catalysts), we believe that some of these vanadium complexes are inactive probably because the imido function is not generated insitu in the presence of aniline.
59. See for example: (a) Susuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. (b) Hill, J. E.; Balaich, G.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1993, 12, 2911. (c) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. (d) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423. (e) van der Linden, A.; Schaverien, C. J.; Meijboom, N.; Ganter, C.; Orpen, A. G. J. Am. Chem. Soc. 1995, 117, 3008.
60. See for example: (a) Susuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. (b) Hill, J. E.; Balaich, G.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1993, 12, 2911. (c) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. (d) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423. (e) van der Linden, A.; Schaverien, C. J.; Meijboom, N.; Ganter, C.; Orpen, A. G. J. Am. Chem. Soc. 1995, 117, 3008.
61. See for example: (a) Susuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. (b) Hill, J. E.; Balaich, G.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1993, 12, 2911. (c) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. (d) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423. (e) van der Linden, A.; Schaverien, C. J.; Meijboom, N.; Ganter, C.; Orpen, A. G. J. Am. Chem. Soc. 1995, 117, 3008.
62. See for example: (a) Susuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. (b) Hill, J. E.; Balaich, G.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1993, 12, 2911. (c) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. (d) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423. (e) van der Linden, A.; Schaverien, C. J.; Meijboom, N.; Ganter, C.; Orpen, A. G. J. Am. Chem. Soc. 1995, 117, 3008.
63. See for example: (a) Susuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. (b) Hill, J. E.; Balaich, G.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1993, 12, 2911. (c) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. (d) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423. (e) van der Linden, A.; Schaverien, C. J.; Meijboom, N.; Ganter, C.; Orpen, A. G. J. Am. Chem. Soc. 1995, 117, 3008.
64. Furthermore, a comparison of the reaction progress (monitored by GC) has also shown complex 2 to be a slightly faster precatalyst than 1.
65. z] produced 85% of imine (M:AM 99:1) in 20 h.
66. 5]. See: Fan, M.; Duesler, E. N.; Paine, R. T. Appl. Organomet. Chem. 2003, 17, 549.
67. 6 and benzophenone), via metathesis, which provides the corresponding imines and titanium oxides.
68. 2/catalyst of 15, and Odom used a ratio of 30 (see also refs 16a and 20).
69. 2: Adams, N.; Cowley, A. R.; Dubberley, S. R.; Sealey, A. J.; Skinner, M. E. G.; Mountford, P. Chem. Commun. 2001, 2738.
70. 2: Adams, N.; Cowley, A. R.; Dubberley, S. R.; Sealey, A. J.; Skinner, M. E. G.; Mountford, P. Chem. Commun. 2001, 2738.
71. 5 is also known to form imido ligands when reacted with primary amines, see: Nugent, W. A.; Harlow, R. L. J. Chem. Soc., Chem. Commun. 1978, 579.
72. In particular, the following organic compounds were identified by GC and GC-MS analyses: formation of the trimers A and B (when using catalyst 3) and an unknown compound C (when using catalyst 5) that was only identified by its molecular mass of 271, corresponding to two hexyne and one benzylamine fragment (this compound may result from a tandem reaction: dimerization of 1-hexyne leading to an enyne followed by its hydroamination).
73. With 3, two isomers of the imine are formed (ratio 3:7). We have not tried to fully identified the isomers and were unable to distinguish which isomer was the major one. We also noticed the formation of the trimers A and B among other side products.
74. Three isomers are formed when using 5 (ratio 2:5:1, mass 203). Although we have not yet tried to fully characterized them, it is conceivable that these three isomers are the Markovnikov imine, the anti-Markovnikov imine, and an enamine product. Compounds A, B, and a compound C′ resulting from the condensation of two hexyne and one α-methylbenzylamine were also formed as side products (mass = 285).
75. Bradley, D. C.; Gitlitz, M. H. J. Chem. Soc. A 1969, 980.
76. Choukroun, R.; Moumboko, P.; Chevalier, S.; Etienne, M.; Donnadieu, B. Angew. Chem., Int. Ed. 1998, 37, 3169.
77. Alyea, E. C.; Bradley, D. C.; Copperthwaite, R. G. J. Chem. Soc., Dalton Trans. 1972, 1580.
78. Altomare, A.; Cascarano, G.; Giacovazzo, G.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
79. Sheldrick, G. M. SHELX97 [includes SHELXS97, SHELXL97, CIFTAB], Programs for Crystal Structure Analysis (Release 97-2); Institüt für Anorganische Chemie: Göttingen, Germany, 1998.
80. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837.
81. Walker, N.; Stuart, D. Acta Crystallogr. A 1983, 39, 158.