Organolanthanide-catalyzed hydroamination/cyclization reactions of aminoalkynes. Computational investigation of mechanism, lanthanide identity, and substituent effects for a very exothermic C-N bond-forming process

Organometallics

Volumn 25, Issue 23, 2006, Pages 5533-5539

  Motta, Alessandro ^a   Fragalà, Ignazio L ^a   Marks, Tobin J ^b  

^a UNIVERSITY OF CATANIA   (Italy)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALKYNES; CYCLIZATION; HYDROAMINATION; ORGANOLANTHANIDES;

CATALYSIS; CHEMICAL BONDS; DISSOCIATION; PROBABILITY DENSITY FUNCTION; RARE EARTH ELEMENTS; SUBSTITUTION REACTIONS;

UNSATURATED COMPOUNDS;

EID: 33751331427     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om060717g     Document Type: Article

References (77)

1. (a) Funke, F.; Steinbrenner, U.; Boehling, R.; Rudolf, P.; Breuer, K.; Hibst, H. Method and catalysts for producing isopropylamine. PCT Int. Appl., 2003.
2. (b) Steinbrenner, U.; Funke, F.; Boehling, R. Method and device for producing ethylamines and butylamines. PCT Int. Appl., 2003.
3. Boehling, R.; Steinbrenner, U.; Funke, F.; Dier, R. Method for producing amines by means of olefin hydroamination in the presence of unsaturated nitrogen compounds. PCT Int. Appl., 2003.
4. Funke, F.; Steinbrenner, U.; Boehling, R. Method for producing dialkylethylamines from dialkylamines and ethylene in the presence of a sodium dialkylamide hydroamination catalyst. PCT Int. Appl., 2003.
5. (e) Boehling, R.; Steinbrenner, U.; Funke, F. Method for the production of n-butyraldehyde and 1-butanol from 1,3-butadiene-containing hydrocarbon streams via hydroamination, isomerization and hydrolysis. PCT Int. Appl., 2003.
6. For general references, see: (a) March, J. Advanced Organic Chemistry, 4th ed.; J. Wiley & Sons: New York, 1992; pp 768-770, and references therein.
7. (b) Brunet, J.-J.; Neibecker, D.; Niedercorn, F. J. Mot. Catal. 1989, 49, 235-259.
8. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; Chapters 1, 4, 7, 17.
9. Trost, B. B.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 8, pp 892-895, and references therein.
10. (e) Gibson, M. S. In The Chemistry of the Amino Croup; Patai, S., Ed.; Interscience: New York, 1968; pp 61-65.
11. For leading reviews of amine additions to olefins and alkynes, see: (a) Beller, M.; Tillack, A.; Seayad, J. Transition Met. Org. Synth. 2004, 2, 403-414.
12. (b) Hegedes, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113-1126.
13. Gase, M.-B.; Latties, A.; Perie, J. J. Tetrahedron 1983, 39, 703-731.
14. Backvall, J.-E. Acc. Chem. Res. 1983, 16, 335-342.
15. (e) Jäger, V.; Viehe, H. G. Houben-Weyl, Methoden der Organischen Chemie; Thieme Velag: Stuttgard, Germany, 1977; Vol. 5/2a, pp 713-724.
16. (f) Suminov, S. I.; Kost, A. N. Russ. Chem. Rev. 1969, 38, 884-899.
17. (g) Chekulaeva, I. A.; Kondraleva, L. V. Russ. Chem. Rev. 1965, 34, 669-680.
18. For hydoamination of alkenes and alkynes mediated by middle and late transition metals, see: (a) Brunet, J.-J.; Neibecker, D.; Philippot, K. Tetrahedron Lett. 1993, 34, 3877-3880.
19. (b) Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z.-I. J. Am. Chem. Soc. 1988, 110, 3994-4002, and references therein.
20. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744.
21. Fukuda, Y.; Utimoto, K.; Nozaki, H. Heterocycles 1987, 25, 297-300.
22. (e) Hegedus, L. S.; Mckearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444-2451.
23. (f) Pugin, B.; Venanzi, L. M. J. Organomet. Chem. 1981, 214, 125-133, and references therein.
24. (g) Barluenga, J.; Azar, F.; Hz, R.; Rodes, R. J. Chem. Soc., Perkin Trans. 1980, 2732-2737.
25. (h) Coulson, D. R. Tetrahedron Lett. 1971, 429-430.
26. Coulson, D. R. U.S. Pat. 3,758,586, 1973.
27. For general organolanthanide reviews, see: (a) (a) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
28. (b) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850.
29. Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896.
30. Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976.
31. (e) Molander, O. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186.
32. (f) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210.
33. (g) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226.
34. (h) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263.
35. Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276.
36. (j) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2.
37. (k) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986.
38. Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362.
39. Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177.
40. (n) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
41. (a) Ryu, J.-S.; Marks, T. J.; McDonald, F. E. J. Org. Chem. 2004, 69, 1038-1052.
42. (b) Ryu, J.-S.; McDonald, F. E.; Marks, T. J. Org. Lett. 2001, 3, 3091-3094.
43. Kim, Y. K.; Livinghouse, T.; Bercaw, J. E. Tetrahedron Lett. 2001, 42, 2933-2935.
44. Molander, G. A.; Dowdy, E. D. J. Org. Chem. 1999, 64, 6515-6517.
45. (e) Molander, G. A.; Dowdy, E. D. J. Org. Chem. 1998, 63, 8983-8988.
46. (a) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275-294.
47. (b) Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108-4109.
48. Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241-10254.
49. Shainyan, B. A.; Mirskova, A. N. Russ. Chem. Rev. 1979, 48, 107-117, and references therein.
50. (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757-1771.
51. (b) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295-9306.
52. Li, Y.; Marks, T. J. Organometallics 1996, 15, 3370-3372.
53. Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708.
54. (e) Li, Y.; Fu, P.-F.; Marks, T. J. Organometallics 1994, 13, 439-440.
55. Motta, A.; Lanza G.; Fragalá, I. L.; Marks, T. J. Organometallics 2004, 23, 4097-4104.
56. Tobisch, S. J. Am Chem. Soc. 2005, 127, 11979-11988.
57. Motta, A.; Fragalá, I. L.; Marks, T. J. Organometallics 2005, 24, 4995-5003.
58. Dolg, M.; Stoll, H.; Savin, A.; Preuss, H. Theor. Chim. Acta 1989, 75, 173-194.
59. Dolg, M.; Stoll, H.; Preuss, H. J. Chem. Phys. 1989, 90, 1730-1734.
60. (a) Eisenstein, O.; Maron, L. J. Organomet. Chem. 2002, 647, 190-197.
61. (b) Maron, L.; Eisenstein, O. J. Phys. Chem. A 2000, 104, 7140-7143.
62. Dolg, M.; Stoll, H. In Handbook of the Physics and Chemistry of Rare Earths; Elsevier Science: Amsterdam, 1996; Vol. 22, pp 607-729.
63. Clark, D. L.; Gordon, J. C.; Hay, P. J.; Martin, R. L.; Poli, R. Organometallics 2002, 21, 5000-5006.
64. (a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972 56, 2257.
65. (b) Franel, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654.
66. Peng, C.; Schlegel, H. B. Isr. J. Chem. 1994, 33, 449-454.
67. (a) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161.
68. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
69. Frisch, M. J.; et al. GAUSSIAN-98; Gaussian Inc.: Pittsburgh, PA, 1995.
70. (a) Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schuman, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091-8103.
71. (b) Klooster, W. T.; Brammer, L.; Schaverien, C. J.; Budzelaar, P. H. M. J. Am. Chem. Soc. 1999, 121, 1381-1382.
72. (a) Chupka, W. A.; Lifshits, C. J. Chem, Phys. 1968, 48, 1109.
73. (b) Kerr, J. A. Chem. Rev. 1966, 66, 465.
74. Shannon, R. D. Acta Crystallogr. 1976, A32, 751-760
75. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334-338.
76. (a) Horton,.A. D. Organometallics 1991, 10, 3910-3918.
77. (b) Burger, B. J.; Thompson, M. E.; Cotter, W. D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 77, 1566-1577.