Copper-catalyzed aerobic oxidative coupling of terminal alkynes with H-phosphonates leading to alkynylphosphonates

Journal of the American Chemical Society

Volumn 131, Issue 23, 2009, Pages 7956-7957

  Gao, Yuxing ^a   Wang, Gang ^a   Chen, Lu ^a   Xu, Pengxiang ^a   Zhao, Yufen ^a,b   Zhou, Yongbo ^c   Han, Li Biao ^a,c  

^a XIAMEN UNIVERSITY   (China)

^b Tsinghua University   (China)

^c NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; COPPER CATALYZED; H-PHOSPHONATES; HIGH YIELD; OXIDATIVE COUPLINGS; TERMINAL ALKYNE;

CHEMICAL REACTIONS;

ACETYLENE;

ALKYNE; COPPER; NITROGEN; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DIMERIZATION; OXIDATION; PHOSPHORYLATION; AEROBIC METABOLISM; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

AEROBIOSIS; ALKYNES; CATALYSIS; COPPER; OXIDATION-REDUCTION; PHOSPHONIC ACIDS;

EID: 67650528785     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9023397     Document Type: Article

References (32)

1. For reviews, see: (a) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
2. (b) Coudray, L.; Montchamp, J. Eur. J. Org. Chem. 2008, 3601.
3. (c) Prim, D.; Campagne, J.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
4. (d) Schwan, A. Chem. Soc. Rev. 2004, 33, 218.
5. (e) Glueck, D. S. Synlett 2007, 2627.
6. (a) Niu, M.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Commun. 2007, 272.
7. (b) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
8. (c) Han, L.-B.; Ono, Y.; Shimada, S. J. Am. Chem. Soc. 2008, 130, 2752.
9. For recent examples, see: (a) Sasaki, S.; Adachi, K.; Yoshifuji, M. Org. Lett. 2007, 9, 1729.
10. (b) Nishida, G.; Noguchi, K.; Hirano, M.; Tanaka, K. Angew. Chem., Int. Ed. 2007, 46, 3951.
11. (c) Ashburn, B. O.; Carter, R. G.; Zakharov, L. N. J. Am. Chem. Soc. 2007, 129, 9109.
12. (d) Heller, B.; Gutnov, A.; Fischer, C.; Drexler, H.; Spannenberg, A.; Redkin, D.; Sundermann, C.; Sundermann, B. Chem. - Eur. J. 2007, 13, 1117.
13. (e) Assema, S.; Jong, G.; Ehlers, A.; Kanter, F.; Schakel, M.; Spek, A.; Lutz, M.; Lammertsma, K. Eur. J. Org. Chem. 2007, 2405.
14. (f) Ben-Valid, S.; Quntar, A.; Srebnik, M. J. Org. Chem. 2005, 70, 3554.
15. (g) Lecercle, D.; Sawicki, M.; Taran, F. Org. Lett. 2006, 8, 4283.
16. (a) Iorga, B.; Eymery, F.; Carmichael, D.; Savignac, P. Eur. J. Org. Chem. 2000, 3103.
17. (b) Lera, M.; Hayes, C. J. Org. Lett. 2000, 2, 3873.
18. (a) Mahajina, M.; Quistad, G. B.; Casida, J. E. Chem. Res. Toxicol. 1996, 9, 241.
19. (b) Van derpoorten, K.; Migaud, M. E. Org. Lett. 2004, 6, 3461.
20. (a) Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422.
21. (b) Hay, A. S. J. Org. Chem. 1962, 27, 3320.
22. (c) Fomina, L.; Vazquez, B.; Tkatchouk, E.; Fomine, S. Tetrahedron 2002, 58, 6741.
23. (d) Eglinton, G.; Galbraith, A. R. J. Chem. Soc. 1959, 889.
24. 2 to form ynamines is known. See: (a) Peterson, L. I. Tetrahedron Lett. 1968, 9, 5357.
25. This reaction can be extended to activated HN compounds. See: (b) Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833.
26. 2P(O)H. See: (a) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
27. (b) Han, L.-B.; Tanaka, M. Shokubai 1999, 41, 577.
28. (a) Sun, X.; Kang, J.; Zhao, Y. Chem. Commun. 2002, 2414.
29. (b) Pokrovsky, A. G.; Pronayeva, T. R.; Fedyuk, N. V.; Shirokova, E. A.; Khandazhinskaya, A. L.; Tarusova, N. B.; Karpenko, I. L.; Krayevsky, A. A. Nucleosides Nucleotides 2001, 20, 1363.
30. 2P(O)OH.
31. (a) Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047.
32. (b) Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev. 2004, 104, 1013.