Palladium-catalyzed synthesis of N-aryl carbamates

Organic Letters

Volumn 15, Issue 6, 2013, Pages 1394-1397

  Vinogradova, Ekaterina V ^a   Park, Nathaniel H ^a   Fors, Brett P ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBAMIC ACID DERIVATIVE; CYANIC ACID DERIVATIVE; PALLADIUM; SODIUM CYANATE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ALCOHOLS; CARBAMATES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYANATES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84875165820     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400369n     Document Type: Article

References (30)

1. Baldinger, S. L.; Shore, E. T. Formulary 1996, 31, 1029
2. Nicolai, E.; Curtet, S.; Sicsic, J.; Lezoualc'h, F.; Fischmeister, R.; Langlois, M.; Maillet, M.; Launay, M. U.S. Patent 7238693, 2007.
3. Li, W.; Li, J.; Wu, Y.; Wu, J.; Hotchandani, R.; Cunningham, K.; McFadyen, I.; Bard, J.; Morgan, P.; Schlerman, F.; Xu, X.; Tam, S.; Goldman, S. J.; Williams, C.; Sypek, J.; Mansour, T. S. J. Med. Chem. 2009, 52, 1799
4. Lee, B. S.; Chun, B. C.; Chung, Y.-C.; Sul, K. I.; Cho, J. W. Macromolecules 2001, 34, 6431
5. Król, P. Prog. Mater. Sci. 2007, 52, 915
6. Kocienski, P. J. In Protecting Groups; Enders, D.; Noyori, R.; Trost, B. M., Eds.; Thieme Foundations of Organic Chemistry Series; Thieme: Stuttgart; New York, 1994; pp 192-209.
7. Chaturvedi, D. Tetrahedron 2012, 68, 15-45 and references therein
8. Perron, V.; Abbott, S.; Moreau, N.; Lee, D.; Penney, C.; Zacharie, B. Synthesis 2008, 283
9. Carpino, L. A. Acc. Chem. Res. 1987, 20, 401
10. Salvatore, R. N.; Shin, S. I.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2001, 66, 1035
11. Keillor, J. W.; Huang, X. Org. Synth. 2002, 78, 234
12. Smith, P. A. S. Org. React. 1946, 3, 337
13. Dubé, P.; Fine Nathel, N. F.; Vetelino, M.; Couturier, M.; Larrivée Aboussafy, C.; Pichette, S.; Jorgensen, M. L.; Hardink, M. Org. Lett. 2009, 11, 5622
14. Wolff, H. Org. React. 1946, 3, 307
15. Paul, F. Coord. Chem. Rev. 2000, 203, 269
16. Tkatchenko, I.; Jaouhari, R.; Bonnet, M.; Dawkins, G.; Lecolier, S. FR2575467, 1986; U.S. Patent 4749806, 1988.
17. Kianmehr, E.; Baghersad, M. H. Adv. Synth. Catal. 2011, 353, 2599
18. Yang, X.; Zhang, Y.; Ma, D. Adv. Synth. Catal. 2012, 354, 2443
19. Vinogradova, E. V.; Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 11132
20. Ueda, S.; Su, M.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 700
21. Kotecki, B. J.; Fernando, D. P.; Haight, A. R.; Lukin, K. A. Org. Lett. 2009, 11, 947
22. Hicks, J. D.; Hyde, A. M.; Cuezva, A. M.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 16720
23. Davis, T. L.; Farnum, J. M. J. Am. Chem. Soc. 1934, 56, 883
24. aza-Wittig cyclyzations: Marsden, S. P.; McGonagle, A. E.; McKeever-Abbas, B. Org. Lett. 2008, 10, 2589
25. Rh(III)-catalyzed amidations: Hesp, K. D.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2011, 133, 11430
26. 1,3-Dipolar cycloadditions: Holt, J.; Fiksdahl, A. J. Heterocycl. Chem. 2007, 44, 375
27. Seymour, R. B.; Kauffman, G. B. J. Chem. Educ. 1992, 69, 909
28. Fields, G. B. In Methods in Molecular Biology, Vol. 35; Pennington, M. W.; Dunn, B. M., Eds.; Humana Press Inc.: Totowa, NJ, 1994; pp 17-27.
29. Jellerichs, B. G.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 7758
30. 2 carbon-halogen bonds at room temperature. Halogen = Cl, Br: Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550