An olefination via ruthenium-catalyzed decarbonylative addition of aldehydes to terminal alkynes

Journal of the American Chemical Society

Volumn 131, Issue 42, 2009, Pages 15092-15093

  Guo, Xiangyu ^a   Wang, Jun ^a   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ALDEHYDES; CHEMICAL EQUATIONS; CHEMO-SELECTIVITY; ELECTRONIC EFFECTS; OLEFINATION; TERMINAL ALKYNE;

ACETYLENE; CHEMICAL REACTIONS; RUTHENIUM;

ALDEHYDES;

ALDEHYDE DERIVATIVE; ALKYNE DERIVATIVE; AROMATIC COMPOUND; CARBON; CHLORIDE ION; POLYMER; RUTHENIUM; WATER;

ADDITION REACTION; ARTICLE; CARBONYLATION; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; DECOMPOSITION; ELECTRON; OLEFINATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 70350279575     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906265a     Document Type: Article

References (31)

1. (a) Kolodiazhnyi, O. I. Phosphorus Ylides: Chemistry and Applications in Organic Chemistry; Wiley-VCH: New York, 1999.
2. (b) Dumeunier, R.; Markó, I. E. In Modern Carbonyl Olefination; Takeda, T., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
3. (a) Hoffmann, R. W. Angew. Chem., Int. Ed. 2001, 40, 1411.
4. (b) Lawrence, N. J. In Preparation of Alkenes: a Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: Oxford, U.K., 1995.
5. For some examples, see: (a) Blasdel, L. K.; Myers, A. G. Org. Lett. 2005, 7, 4281.
6. (b) Lattanzi, A.; Orelli, L. R.; Barone, P.; Massa, A.; Iannece, P.; Scettri, A. Tetrahedron Lett. 2003, 44, 1333.
7. (c) Comins, D. L.; Ollinger, C. G. Tetrahedron Lett. 2001, 42, 4115.
8. For some examples, see: (a) Huang, J.; Wu, C.; Wulff, W. D. J. Am. Chem. Soc. 2007, 129, 13366.
9. (b) Aubele, D. L.; Wan, S.; Floreancig, P. E. Angew. Chem., Int. Ed. 2005, 44, 3485.
10. (c) Kano, N.; Kawashima, T. In Modern Carbonyl Olefination; Takeda, T., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
11. For some examples, see: (a) Aissa, C. Eur. J. Org. Chem. 2009, 1831.
12. (b) Calata, C.; Catel, J.-M.; Pfund, E.; Lequeux, T. Tetrahedron 2009, 65, 3967.
13. (c) Allen, J. V.; Green, A. P.; Hardy, S.; Heron, N. M.; Lee, A. T. L.; Thomas, E. J. Tetrahedron Lett. 2008, 49, 6352.
14. For some examples, see: (a) Jung, M. E.; Pontillo, J. Tetrahedron 2003, 59, 2729.
15. (b) Hartley, R. C.; McKiernan, G. J. J. Chem. Soc., Perkin Trans. 1 2002, 2763.
16. (a) Trost, B. M. Science 1991, 254, 1471.
17. (b) Trost, B. M. Angew. Chem., Int. Ed. 1995, 34, 259.
18. (c) Li, C.-J.; Trost, B. M. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 13197.
19. For some examples, see: (a) Alcaide, B.; Almendros, P.; Luna, A. Chem. Rev. 2009, 109, 3817.
20. (b) Vehlow, K.; Wang, D.; Buchmeiser, M. R.; Blechert, S. Angew. Chem., Int. Ed. 2008, 47, 2615.
21. (c) Clark, D. A.; Clark, J. R.; Diver, S. T. Org. Lett. 2008, 10, 2055.
22. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
23. (e) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 3975.
24. (f) Chauvin, Y.; Gilbert, B.; Guibard, I. Chem. Commun. 1990, 1715.
25. (g) Schrock, R. R.; Meakin, P. J. Am. Chem. Soc. 1974, 96, 5288.
26. (a) Iwai, T.; Fujihara, T.; Tsuji, Y. Chem. Commun. 2008, 6215.
27. (b) Kreis, M.; Palmelund, A.; Bunch, L.; Madsen, R. Adv. Synth. Catal. 2006, 348, 2148.
28. (c) Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Am. Chem. Soc. 2002, 124, 3806.
29. (a) Jun, C.-H.; Jo, E.-A.; Park, J.-W. Eur. J. Org. Chem. 2007, 1869.
30. (b) Kondo, T.; Okada, T.; Mitsudo, T. Organometallics 1999, 18, 4123.
31. Please see the Supporting Information.