Unprecedented synthesis of alkynylphosphine-boranes through room-temperature oxidative alkynylation

Organic Letters

Volumn 15, Issue 17, 2013, Pages 4592-4595

  Jouvin, Kévin ^a   Veillard, Romain ^b   Theunissen, Cédric ^c   Alayrac, Carole ^b   Gaumont, Annie Claude ^b   Evano, Gwilherm ^c  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

^b UNIVERSITÉ DE CAEN   (France)

^c UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84883786467     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402197d     Document Type: Article

References (32)

1. Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 2010, 49, 2840
2. DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064
3. Evano, G.; Jouvin, K.; Coste, A. Synthesis 2013, 45, 17
4. Witulski, B.; Alayrac, C. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; de Meijere, A., Ed.; Thieme: Stuttgart, 2005; Vol. 24, pp 933-956.
5. Potapov, V. A.; Trofimov, B. A. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; de Meijere, A., Ed.; Thieme: Stuttgart, 2005; Vol. 24, pp 957-1005.
6. Pietrusiewicz, K. M.; Stankević, M. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; de Meijere, A., Ed.; Thieme: Stuttgart, 2005; Vol. 24, pp 1073-1086.
7. Kondoh, A.; Yorimitsu, H.; Oshima, K. Chem.-Asian J. 2010, 5, 398
8. Bernoud, E.; Veillard, R.; Alayrac, C.; Gaumont, A.-C. Molecules 2012, 17, 14573
9. Imamoto, T.; Saitoh, Y.; Koide, A.; Ogura, T.; Yoshida, K. Angew. Chem., Int. Ed. 2007, 46, 8636
10. Ochida, A.; Ito, H.; Sawamura, M. J. Am. Chem. Soc. 2006, 106, 16486
11. Ito, H.; Ohmiya, H.; Sawamura, M. Org. Lett. 2010, 12, 4380
12. Charrier, C.; Chodkiewicz, W.; Cadiot, P. Bull. Soc. Chim. Fr. 1966, 1002
13. Ortial, S.; Montchamp, J.-L. Org. Lett. 2011, 13, 3134
14. Bernoud, E.; Alayrac, C.; Delacroix, O.; Gaumont, A.-C. Chem. Commun. 2011, 47, 3239
15. Abdellah, I.; Bernoud, E.; Lohier, J.-F.; Alayrac, C.; Gaumont, A.-C.; Toupet, L.; Lepetit, C. Chem. Commun. 2012, 48, 4088
16. Beletskaya, I. P.; Afanasiev, V. V.; Kazankova, M. A.; Efimova, I. V. Org. Lett. 2003, 5, 4309
17. Afanasiev, V. V.; Beletskaya, I. P.; Kazankova, M. A.; Efimova, I. V.; Antipin, M. U. Synthesis 2003, 2835
18. Gao, Y.; Wang, G.; Chen, L.; Xu, P.; Zhao, Y.; Zhou, Y.; Han, L.-B. J. Am. Chem. Soc. 2009, 131, 7956
19. Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Angew. Chem., Int. Ed. 2009, 48, 4381
20. Jouvin, K.; Couty, F.; Evano, G. Org. Lett. 2010, 12, 3272
21. Laouiti, A.; Rammah, M. M.; Rammah, M. B.; Marrot, J.; Couty, F.; Evano, G. Org. Lett. 2012, 14, 6
22. Jouvin, K.; Bayle, A.; Legrand, F.; Evano, G. Org. Lett. 2012, 14, 1652
23. Jouvin, K.; Coste, A.; Bayle, A.; Legrand, F.; Karthikeyan, G.; Tadiparthi, K.; Evano, G. Organometallics 2012, 31, 7933
24. Jouvin, K.; Heimburger, J.; Evano, G. Chem. Sci. 2012, 3, 756
25. Laouiti, A.; Jouvin, K.; Rammah, M. M.; Rammah, M. B.; Evano, G. Synthesis 2012, 44, 1491
26. Aves, S. J.; Spring, D. R. In Patai Series: The Chemistry of Functional Groups. The Chemistry of Organocopper Compounds; Rappoport, Z.; Marek, I., Eds.; John Wiley & Sons Ltd.: Chichester, 2009; Vol. 24, pp 585-602.
27. Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244
28. Gaumont, A.-C.; Carboni, B. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Kaufmann, D. E.; Matteson, D. S., Eds.; Thieme: Stuttgart, 2005; Vol. 6, pp 485-512.
29. Gelman, D.; Jiang, L.; Buchwald, S. L. Org. Lett. 2003, 5, 2315
30. Li, Y.; Das, S.; Zhou, S.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2012, 134, 9727
31. Brisset, H.; Gourdel, Y.; Pellon, P.; Le Corre, M. Tetrahedron Lett. 1993, 34, 4523
32. Uziel, J.; Darcel, C.; Moulin, D.; Bauduin, C.; Jugé, S. Tetrahedron: Asymmetry 2001, 12, 1441