Phosphoramidate synthesis via copper-catalysed aerobic oxidative coupling of amines and H-phosphonates

Chemical Communications

Volumn 49, Issue 79, 2013, Pages 8919-8921

  Fraser, Jamie ^a   Wilson, Laura J ^a   Blundell, Rebecca K ^a   Hayes, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AMINES; CATALYSIS; COPPER; ORGANOPHOSPHONATES; OXIDATIVE COUPLING; OXYGEN; PHOSPHORIC ACIDS;

AMINE; ANILINE; BENZALDEHYDE; COPPER; OXYGEN; PHENYLALANINE METHYL ESTER; PHOSPHONIC ACID DERIVATIVE; PHOSPHORAMIDIC ACID;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; OXIDATION; OXIDATIVE COUPLING; PURIFICATION; STEREOSPECIFICITY; SYNTHESIS;

EID: 84883874823     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc45680c     Document Type: Article

References (27)

1. D. R. Phillips, M. Uramoto, K. Isono, A. McCloskey, J. Org. Chem., 1993, 58, 854
2. W. P. Roberts, M. E. Tate, A. Kerr, Nature, 1977, 265, 379
3. M. E. Tate, P. J. Murphy, W. P. Roberts, A. Kerr, Nature, 1979, 265, 697
4. J. I. Guijarro, J. E. González-Pastor, F. Baleux, J. L. S. Millán, M. A. Castilla, M. Rico, F. Moreno, M. Delepierre, J. Biol. Chem., 1995, 270, 23520
5. J. J. Hale, S. G. Mills, M. MacCoss, C. P. Dorn, P. E. Finke, R. J. Budhu, R. A. Reamer, S.-E. W. Huskey, D. Luffer-Atlas, B. J. Dean, E. M. McGowan, W. P. Feeney, S.-H. L. Chiu, M. A. Cascieri, G. G. Chicchi, M. M. Kurtz, S. Sadowski, E. Ber, F. D. Tattersall, N. M. J. Rupniak, A. R. Williams, W. Rycroft, R. Hargreaves, J. M. Metzger, D. E. MacIntyre, J. Med. Chem., 2000, 43, 1234
6. M. Serpi, R. Bibbo, S. Rat, H. Roberts, C. Hughes, B. Caterson, M. J. Alcaraz, A. T. Gibert, C. R. A. Verson, C. McGuigan, J. Med. Chem., 2012, 55, 4629
7. T.-M. Nguyen, S. C. Chang, B. Condon, R. Slopek, E. Graves, M. Yoshioka-Tarver, Ind. Eng. Chem. Res., 2013, 52, 4715
8. T.-M. D. Nguyen, S. C. Chang, B. Condon, M. Uchimiya, C. Fortier, Polym. Adv. Technol., 2012, 23, 1555
9. X. Gao, Z. Tang, M. Lu, H. Liu, Y. Jiang, Y. Zhaoc, Z. Cai, Chem. Commun., 2012, 48, 10198
10. F. R. Atherton, H. T. Openshaw, A. R. Todd, J. Chem. Soc., 1945, 660
11. R. L. Letsinger, M. E. Schott, J. Am. Chem. Soc., 1981, 103, 7394
12. J. Nielsen, M. H. Caruthers, J. Am. Chem. Soc., 1988, 110, 6275
13. I. Wilkening, G. del Signore, C. P. R. Hackenberger, Chem. Commun., 2008, 2932
14. R. Serwa, P. Majkut, B. Horstmann, J.-M. Swiecicki, M. Gerrits, E. Krause, C. P. R. Hackenberger, Chem. Sci., 2010, 1, 596
15. W. Xiao, C.-Y. Zhou, C.-M. Che, Chem. Commun., 2012, 48, 5871
16. W. Shi, C. Liu, A. Lei, Chem. Soc. Rev., 2011, 40, 2761
17. K. Hirano, M. Miura, Chem. Commun., 2012, 48, 10704
18. T. Hamada, X. Ye, S. S. Stahl, J. Am. Chem. Soc., 2008, 130, 833
19. X. Jin, K. Yamaguchi, N. Mizuno, Chem. Commun., 2012, 48, 4974
20. Y. Gao, G. Wang, L. Chen, P. Xu, Y. Zhao, Y. Zhou, L.-B. Han, J. Am. Chem. Soc., 2009, 131, 7956
21. L. Wang, H. Huang, D. L. Priebbenow, F.-F. Pan, C. Bolm, Angew. Chem., Int. Ed., 2013, 52, 3478
22. D. J. C. Constable, P. J. Dunn, J. D. Hayler, G. R. Humphrey, J. L. Leazer Jr., R. J. Linderman, K. Lorenz, J. Manley, B. A. Pearlman, A. Wells, A. Zaksh, T. Y. Zhang, Green Chem., 2007, 9, 411
23. X. Jin, K. Yamaguchi, N. Mizuno, Org. Lett., 2013, 15, 418
24. R. D. Patil, S. Adimurthy, Adv. Synth. Catal., 2011, 353, 1695
25. Y. Zhou, S. Yin, Y. Gao, Y. Zhao, M. Goto, L.-B. Han, Angew. Chem., Int. Ed., 2010, 49, 6852
26. C. McGuigan, P. Murziani, M. Slusarczyk, B. Gonczy, J. V. Voorde, S. Liekens, J. Balzarini, J. Med. Chem., 2011, 54, 7247
27. L. Chu, F.-L. Qing, J. Am. Chem. Soc., 2010, 132, 7262