Introducing a new class of N-phosphoryl ynamides via Cu(I)-catalyzed amidations of alkynyl bromides

Organic Letters

Volumn 13, Issue 18, 2011, Pages 4862-4865

  Dekorver, Kyle A ^a   Walton, Mary C ^a   North, Troy D ^a   Hsung, Richard P ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BROMINATED HYDROCARBON; COPPER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMIDES; CATALYSIS; COPPER; CRYSTALLOGRAPHY, X-RAY; HYDROCARBONS, BROMINATED; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 80052762591     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201947b     Document Type: Article

References (46)

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. Balieu, S.; Toutah, K.; Carro, L.; Chamoreau, L.-M.; Rouselière, H.; Courillon, C. Tetrahedron Lett. 2011, 52, 2876
4. Fadel, A.; Legrand, F.; Evano, G.; Rabasso, N. Adv. Synth. Catal. 2011, 353, 263
5. Schotes, C.; Mezzetti, A. Angew. Chem. 2011, 123, 3128
6. Barbazanges, M.; Meyer, C.; Cossy, J.; Turner, P. Chem.-Eur. J. 2011, 17, 4480
7. Pizzetti, M.; Russo, A.; Petricci, E. Chem.-Eur. J. 2011, 17, 4523
8. Garcia, P.; Evanno, Y.; George, P.; Sevrin, M.; Ricci, G.; Malacria, M.; Aubert, C.; Gandon, V. Org. Lett. 2011, 13, 2030
9. Kramer, S.; Friis, S. D.; Xin, Z.; Odabachian, Y.; Skrydstrup, T. Org. Lett. 2011, 13, 1750
10. Li, C.; Zhang, L. Org. Lett. 2011, 13, 1738
11. Wang, Y. P.; Danheiser, R. L. Tetrahedron Lett. 2011, 52, 2111
12. Mak, X, Y.; Crombie, A. L.; Danheiser, R. L. J. Org. Chem. 2011, 76, 1852
13. Davies, P. W.; Cremonesi, A.; Martin, N. Chem. Commun. 2011, 379
14. Xu, C.-F.; Mei, Xu, M.; Jia, Y. X.; Li, C.-Y. Org. Lett. 2011, 13, 1556
15. Chen, Z.; Zheng, D.; Wu, J. Org. Lett. 2011, 13, 848
16. Shindoh, N.; Takemoto, Y.; Takasu, K. Heterocycles 2011, 82, 1133
17. Saito, N.; Katayama, T.; Saito, K. Heterocycles 2011, 82, 1181
18. Kramer, S.; Odabachian, Y.; Overgaard, J.; Rottländer, M.; Gagosz, F.; Skrydstrup, T. Angew. Chem. 2011, 123, 5196
19. Nissen, F.; Richard, V.; Alayrac, C.; Witulski, B. Chem. Commun. 2011, 47, 6656
20. Hashmi, A. S. K.; Schuster, A. M.; Zimmer, M.; Rominger, F. Chem.-Eur. J. 2011, 17, 5511
21. Gilboa, N.; Wang, H.; Houk, K. N.; Marek, I. Chem.-Eur. J. 2011, 17, 8000
22. Chemla, F.; Dulong, F.; Ferreira, F.; Nüllen, M. P.; Pérez-Luna, A. Synthesis 2011, 9, 1347
23. Saito, N.; Saito, K.; Shiro, M.; Sato, Y. Org. Lett. 2011, 13, 2718
24. Tracey, M. R.; Hsung, R. P.; Antoline, J. A.; Kurtz, K. C. M.; Shen, L.; Slafer, B. W.; Zhang, Y. In Science of Synthesis, Houben-Weyl Methods of Molecular Transformations; Weinreb, S. M., Ed.; Georg Thieme Verlag KG: Stuttgart, Germany, 2005; Chapter 21.4.
25. Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379
26. Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405
27. Sueda, T.; Oshima, A.; Teno, N. Org. Lett. 2011, 13, 3996
28. 2-C and phosphoramidate, see: Yang, T.; Lin, C.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2005, 7, 4781
29. Jeng, A. Y.; De Lombaert, S. Curr. Pharm. Des. 1997, 3, 597
30. Colvin, O. M. Curr. Pharm. Des. 1999, 5, 555-8
31. Milzner, K.; Reisser, F. Patent CH 554376, 1974.
32. Anderson, J.; Homeyer, B.; Kuehle, E.; Scheinpflug, H.; Zeck, W. M.; Simonet, D. E. Patent US 4603214, 1986.
33. Zhang, Y.; DeKorver, K. A.; Lohse, A. G.; Zhang, Y.-S.; Huang, J.; Hsung, R. P. Org. Lett. 2009, 11, 899
34. DeKorver, K. A.; Hsung, R. P.; Lohse, A. G.; Zhang, Y. Org. Lett. 2010, 12, 1840
35. DeKorver, K. A.; North, T. D.; Hsung, R. P. Synlett 2010, 2397
36. DeKorver, K. A.; Johnson, W. L.; Zhang, Y.; Hsung, R. P.; Dai, H.; Deng, J.; Lohse, A. G.; Zhang, Y.-S. J. Org. Chem. 2011, 76, 5092
37. Garrison, A. W.; Boozer, C. E. J. Am. Chem. Soc. 1968, 90, 3486
38. Núñez, A.; Berroterán, D.; Núñez, O. Org. Biomol. Chem. 2003, 1, 2283
39. For a review of ketenimine cycloadditions, see: Alajarin, M.; Vidal, A.; Tovar, F. Targets Heterocycl. Syst. 2000, 4, 293
40. Arnold, B.; Regitz, M. Angew. Chem., Int. Ed. 1979, 4, 320
41. Van Camp, A.; Goosens, D.; Moya-Portuguez, M.; Marchand-Brynaert, J.; Ghosez, L. Tetrahedron Lett. 1980, 21, 3081
42. Alajarin, M.; Molina, P.; Vidal, A. Tetrahedron Lett. 1996, 37, 8945
43. Whiting, M.; Fokin, V. V. Angew. Chem., Int. Ed. 2006, 45, 3157
44. Molt, O.; Schrader, T. Synthesis 2002, 2633
45. McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239
46. Thomas, C. D.; McParland, J. P.; Hanson, P. R. Eur. J. Org. Chem. 2009, 32, 5487