Direct observation of oxidative cyclization of η2-alkene and η2-aldehyde on Ni(0) center. Significant acceleration by addition of Me3SiOTf

Journal of the American Chemical Society

Volumn 126, Issue 38, 2004, Pages 11802-11803

  Ogoshi, Sensuke ^a   Oka, Masa Aki ^a   Kurosawa, Hideo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; ALUMINUM DERIVATIVE; CARBON; LEWIS ACID; LIGAND; METAL; NICKEL; OXYGEN; PALLADIUM; SILANE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; X RAY DIFFRACTION;

EID: 4644370089     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0460716     Document Type: Article

References (27)

1. Acetylene: (a) Oblinger, E.; Montgomery, J.; J. Am. Chem. Soc. 1997, 119, 9065-9066.
2. (b) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 725, 3442-3443.
3. (c) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 726, 3698-3699.
4. Diene: (d) Takimoto, M.; Hiraga, Y.; Sato, Y.; Mori, M. Tetrahedron Lett. 1998, 39, 4543-4546.
5. (e) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 720, 4033-4034.
6. (f) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem, Int. Ed. 1999, 38, 397-400.
7. Allene: (g) Rang, S.; Yoon, S. Chem. Commun. 2002, 2634-2635.
8. Review: (h) Montgomery, J. Angew. Chem, Int. Ed. 2004, 43, 3890-3908.
9. Oxidative cyclization of C=O and C=C with Ti(II): Hewlett, D. F.; Whitby, R. J. Chem. Commun. 1990, 1684-1686. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785-6786. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787-6788. Quan, L. G.; Cha, J. K. Tetrahedron Lett. 2001, 42, 8567-8569. Nickelacycles derived from oxidative cyclization: Hoberg, H.; Peres, Y.; Krüger, C.; Tasy, Y.-H. Angew. Chem, Int. Ed. Engl. 1987, 26, 771-773. Walther, D.; Dinjus, E.; Sieler, J.; Andersen, L.; Lindqvist, O. J. Organomet. Chem, 1984, 276, 99-107. Walther, D.; Bräunlich, G.; Kempe, R.; Sieler, J. J. Organomet. Chem. 1992, 436, 109-119. Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370-372.
10. Oxidative cyclization of C=O and C=C with Ti(II): Hewlett, D. F.; Whitby, R. J. Chem. Commun. 1990, 1684-1686. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785-6786. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787-6788. Quan, L. G.; Cha, J. K. Tetrahedron Lett. 2001, 42, 8567-8569. Nickelacycles derived from oxidative cyclization: Hoberg, H.; Peres, Y.; Krüger, C.; Tasy, Y.-H. Angew. Chem, Int. Ed. Engl. 1987, 26, 771-773. Walther, D.; Dinjus, E.; Sieler, J.; Andersen, L.; Lindqvist, O. J. Organomet. Chem, 1984, 276, 99-107. Walther, D.; Bräunlich, G.; Kempe, R.; Sieler, J. J. Organomet. Chem. 1992, 436, 109-119. Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370-372.
11. Oxidative cyclization of C=O and C=C with Ti(II): Hewlett, D. F.; Whitby, R. J. Chem. Commun. 1990, 1684-1686. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785-6786. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787-6788. Quan, L. G.; Cha, J. K. Tetrahedron Lett. 2001, 42, 8567-8569. Nickelacycles derived from oxidative cyclization: Hoberg, H.; Peres, Y.; Krüger, C.; Tasy, Y.-H. Angew. Chem, Int. Ed. Engl. 1987, 26, 771-773. Walther, D.; Dinjus, E.; Sieler, J.; Andersen, L.; Lindqvist, O. J. Organomet. Chem, 1984, 276, 99-107. Walther, D.; Bräunlich, G.; Kempe, R.; Sieler, J. J. Organomet. Chem. 1992, 436, 109-119. Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370-372.
12. Oxidative cyclization of C=O and C=C with Ti(II): Hewlett, D. F.; Whitby, R. J. Chem. Commun. 1990, 1684-1686. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785-6786. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787-6788. Quan, L. G.; Cha, J. K. Tetrahedron Lett. 2001, 42, 8567-8569. Nickelacycles derived from oxidative cyclization: Hoberg, H.; Peres, Y.; Krüger, C.; Tasy, Y.-H. Angew. Chem, Int. Ed. Engl. 1987, 26, 771-773. Walther, D.; Dinjus, E.; Sieler, J.; Andersen, L.; Lindqvist, O. J. Organomet. Chem, 1984, 276, 99-107. Walther, D.; Bräunlich, G.; Kempe, R.; Sieler, J. J. Organomet. Chem. 1992, 436, 109-119. Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370-372.
13. Oxidative cyclization of C=O and C=C with Ti(II): Hewlett, D. F.; Whitby, R. J. Chem. Commun. 1990, 1684-1686. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785-6786. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787-6788. Quan, L. G.; Cha, J. K. Tetrahedron Lett. 2001, 42, 8567-8569. Nickelacycles derived from oxidative cyclization: Hoberg, H.; Peres, Y.; Krüger, C.; Tasy, Y.-H. Angew. Chem, Int. Ed. Engl. 1987, 26, 771-773. Walther, D.; Dinjus, E.; Sieler, J.; Andersen, L.; Lindqvist, O. J. Organomet. Chem, 1984, 276, 99-107. Walther, D.; Bräunlich, G.; Kempe, R.; Sieler, J. J. Organomet. Chem. 1992, 436, 109-119. Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370-372.
14. Oxidative cyclization of C=O and C=C with Ti(II): Hewlett, D. F.; Whitby, R. J. Chem. Commun. 1990, 1684-1686. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785-6786. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787-6788. Quan, L. G.; Cha, J. K. Tetrahedron Lett. 2001, 42, 8567-8569. Nickelacycles derived from oxidative cyclization: Hoberg, H.; Peres, Y.; Krüger, C.; Tasy, Y.-H. Angew. Chem, Int. Ed. Engl. 1987, 26, 771-773. Walther, D.; Dinjus, E.; Sieler, J.; Andersen, L.; Lindqvist, O. J. Organomet. Chem, 1984, 276, 99-107. Walther, D.; Bräunlich, G.; Kempe, R.; Sieler, J. J. Organomet. Chem. 1992, 436, 109-119. Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370-372.
15. Oxidative cyclization of C=O and C=C with Ti(II): Hewlett, D. F.; Whitby, R. J. Chem. Commun. 1990, 1684-1686. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785-6786. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787-6788. Quan, L. G.; Cha, J. K. Tetrahedron Lett. 2001, 42, 8567-8569. Nickelacycles derived from oxidative cyclization: Hoberg, H.; Peres, Y.; Krüger, C.; Tasy, Y.-H. Angew. Chem, Int. Ed. Engl. 1987, 26, 771-773. Walther, D.; Dinjus, E.; Sieler, J.; Andersen, L.; Lindqvist, O. J. Organomet. Chem, 1984, 276, 99-107. Walther, D.; Bräunlich, G.; Kempe, R.; Sieler, J. J. Organomet. Chem. 1992, 436, 109-119. Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370-372.
16. Oxidative cyclization of C=O and C=C with Ti(II): Hewlett, D. F.; Whitby, R. J. Chem. Commun. 1990, 1684-1686. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785-6786. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787-6788. Quan, L. G.; Cha, J. K. Tetrahedron Lett. 2001, 42, 8567-8569. Nickelacycles derived from oxidative cyclization: Hoberg, H.; Peres, Y.; Krüger, C.; Tasy, Y.-H. Angew. Chem, Int. Ed. Engl. 1987, 26, 771-773. Walther, D.; Dinjus, E.; Sieler, J.; Andersen, L.; Lindqvist, O. J. Organomet. Chem, 1984, 276, 99-107. Walther, D.; Bräunlich, G.; Kempe, R.; Sieler, J. J. Organomet. Chem. 1992, 436, 109-119. Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370-372.
17. It was suggested that the coordination of a Lewis acidic reagent to a carbonyl group on nickel enhances the reactivity of the carbonyl compound.1f
18. 1: C, 65.92; H, 9.91. Found: C, 64.99; H, 9.64.
19. 0.5 C, 71.01; H, 8.84. Found: C, 70.60; H, 8.91.
20. Similar carbonylation of titanium complexes has been reported: (a) Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557-1558.
21. (b) Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818-5819.
22. 2), 6.80-7.10 (br, 11H, including -CHO).
23. Ogoshi, S.; Yoshida, T.; Nishida, T.; Monta, M.; Kurosawa, H. J. Am. Chem. Soc. 2001, 123, 1944-1950. Ogoshi, S.; Tomiyasu, S.; Morita, M.; Kurosawa, H. J. Am. Chem. Soc. 2002, 124, 11598-11599.
24. Ogoshi, S.; Yoshida, T.; Nishida, T.; Monta, M.; Kurosawa, H. J. Am. Chem. Soc. 2001, 123, 1944-1950. Ogoshi, S.; Tomiyasu, S.; Morita, M.; Kurosawa, H. J. Am. Chem. Soc. 2002, 124, 11598-11599.
25. 1: C, 54.32; H, 7.41. Found: C, 54.08; H, 7.38.
26. Walther, D. J. Organomet. Chem. 1980. 790, 393-401.
27. 6): δ 42.0 (s).