Cobalt-catalyzed [2+2] cycloaddition

Angewandte Chemie - International Edition

Volumn 47, Issue 36, 2008, Pages 6811-6813

  Treutwein, Jonas ^a   Hilt, Gerhard ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Alkenes; Alkynes; Cobalt; Cycloaddition

Indexed keywords

ACETYLENE; CHEMICAL REACTIONS; COBALT; COMPLEXATION; DIFFERENCE EQUATIONS; HYDROCARBONS; MATHEMATICAL TRANSFORMATIONS; PROPANE; SYNTHESIS (CHEMICAL);

[2 + 2] CYCLOADDITION; ALKENES; ALKYNES; CHEMICAL EQUATIONS; CHEMO-SELECTIVE; CYCLO BUTENE; CYCLOADDITION; DIPHOSPHINE; EXCELLENT YIELDS; SYNTHESIS OF;

TRANSITION METALS;

EID: 53249086533     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801778     Document Type: Article

References (32)

1. For leading studies, see: Y. Takenaka, H. Ito, M. Hasegawa, K. Iguchi, Tetrahedron 2006, 62, 3380 ;
2. N. P. Tsvetkov, A. B. Koldobskii, V. N. Kalinin, Dokl. Chem. 2005, 404, 174, and references therein.
3. R. R. Burton, W. Tam, J. Org. Chem. 2007, 72, 7333 ;
4. K. Villeneuve, N. Riddell, W. Tam, Tetrahedron 2006, 62, 3823;
5. N. Riddell, W. Tam, J. Org. Chem. 2006, 71, 1934;
6. P. Liu, R. W. Jordan, S. P. Kibbee, J. D. Goddard, W. Tam, J. Org. Chem. 2006, 71, 3793;
7. N. Riddell, K. Villeneuve, W. Tam, Org. Lett. 2005, 7, 3681;
8. F. M. Pfeffer, T. Gunnlaugsson, P. Jensen, P. E. Kruger, Org. Lett. 2005, 7, 5357;
9. K. Villeneuve, W. Tam, Angew. Chem. 2004, 116, 620;
10. Angew. Chem. Int. Ed. 2004, 43, 610;
11. A. Tenaglia, L. Giordano, Synlett 2003, 2333;
12. K. Villeneuve, R. W. Jordan, W. Tam, Synlett 2003, 2123;
13. P. Alvarez, J. Gimeno, E. Lastra, S. Garzía-Granda, J. F. van der Maelen, M. Bassetti, Organometallics 2001, 20, 3762;
14. R. W. Jordan, W. Tam, Org. Lett. 2000, 2, 3031;
15. T.-a. Mitsudo, H. Naruse, T. Kondo, Y. Ozaki, Y. Watanabe, Angew. Chem. 1994, 106, 595;
16. Angew. Chem. Int. Ed. Engl. 1994, 33, 580;
17. R. N. Warrener, G. Abbenante, R. G. Solomon, R. A. Russell, Tetrahedron Lett. 1994, 35, 7639.
18. T. Shibata, K. Takami, A. Kawachi, Org. Lett. 2006, 8, 1343.
19. D. K. Rayabarapu, C.-H. Cheng, Acc. Chem. Res. 2007, 40, 971;
20. K. C. Chao, D. K. Rayabarapu, C.-C. Wang, C.-H. Cheng, J. Org. Chem. 2001, 66, 8804;
21. for a leading study on nickel-catalyzed [2+2] cycloaddition, see: D. J. Huang, L. P. Li, D. K. Rayabarapu, T. Sambaiah, C.-H. Cheng, Chem. Eur. J. 2000, 6, 3706.
22. G. Hilt, J. Treutwein, Angew. Chem. 2007, 119, 8653;
23. Angew. Chem. Int. Ed. 2007, 46, 8500.
24. For leading studies, see: B. M. Trost, M. U. Frederiksen, M. D. Rudd, Angew. Chem. 2005, 117, 6788;
25. Angew. Chem. Int. Ed. 2005, 44, 6630;
26. B. M. Trost, Acc. Chem. Res. 2002, 35, 695;
27. B. M. Trost, H. C. Shen, A. B. Pinkerton, Chem. Eur. J. 2002, 8, 2341;
28. B. M. Trost, M. Machacek, M. J. Schnaderbeck, Org. Lett. 2000, 2, 1761;
29. B. M. Trost, J. A. Martinez, R. J. Kulawiec, A. F. Indolese, J. Am. Chem. Soc. 1993, 115, 10402.
30. A relatively slow cyclotrimerization of the internal alkyne was observed as an alternative reaction pathway with 1,4-dimethoxy-2-butyne. When a slight excess of the alkyne component was used, the alkene underwent complete conversion,and the desired product could be purified by simple filtration through a plug of silica gel.
31. It seems that in the context of the cobalt-catalyzed [2+2] cycloaddition reaction,only the exo products with respect to the cyclobutene ring are generated,as confirmed by NMR spectroscopy and X-ray crystal-structure analysis.
32. For an iron-catalyzed [2+2] cycloaddition with simple alkenes, see: M. Rosenblum, D. Scheck, Organometallics 1982, 1, 397.