Synthesis of acyl carbamates via four component Pd-catalyzed carbonylative coupling of aryl halides, potassium cyanate, and alcohols

Organic Letters

Volumn 17, Issue 5, 2015, Pages 1248-1251

  Yin, Hongfei ^a   De Almeida, Angelina M ^a,b   De Almeida, Mauro V ^b   Lindhardt, Anders T ^a   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b FEDERAL UNIVERSITY OF JUIZ DE FORA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; AMMONIA; CARBAMIC ACID DERIVATIVE; CYANIC ACID DERIVATIVE; HALOGENATED HYDROCARBON; PALLADIUM; POTASSIUM CYANATE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALCOHOLS; AMIDES; AMMONIA; CARBAMATES; CATALYSIS; CYANATES; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84924275665     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00221     Document Type: Article

References (52)

1. Thulam, V. K.; Kotte, S. C. B.; Sanjay Kumar, H. J. Pharm. Res. 2013, 7, 195
2. Davidovich, C.; Bashan, A.; Auerbach-Nevo, T. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 4291
3. Picard, J. A.; O-Brien, P. M.; Sliskovic, D. R. J. Med. Chem. 1996, 39, 1243
4. Kahns, A. H.; Bundgaard, H. Int. J. Pharm. 1991, 71, 31
5. Fraser, J.; Clinch, P.; Reay, R. J. Sci. Food. Agr. 1965, 16, 615
6. Bourbon, P.; Peng, Q.; Ferraudi, G. Bioorg. Med. Chem. Lett. 2013, 23, 6321
7. Shaw-Ponter, S.; Mills, G.; Robertson, M. Tetrahedron Lett. 1996, 37, 1867
8. Young, R. J.; Shaw-Ponter, S.; Hardy, G. W. Tetrahedron Lett. 1994, 35, 8687
9. Urano, S.; Yabuta, M. U.S. Patent 5,892,100, 1999.
10. Bach, A.; Gether, U.; Stromgaard, K. Org. Biomol. Chem. 2010, 8, 4281
11. Damon, D. B.; Scott, J. M.; Scott, R. W. Org. Process Res. Dev. 2006, 10, 472
12. Li, K. L.; Cheng, X. H.; Hii, H. H. Eur. J. Org. Chem. 2004, 5, 959
13. Kim, M. K.; Cho, S. Y.; Chong, Y. H. Bioorg. Med. Chem. 2014, 22, 1156
14. Martinelli, F.; Palmieri, A.; Petrini, M. Eur. J. Org. Chem. 2010, 2010, 5085
15. Nevill, C. R., Jr; Angell, P. T. Tetrahedron Lett. 1998, 39, 5671
16. Kashima, C.; Arao, H. J. Heterocycl. Chem. 1991, 28, 805
17. Nair, V.; Mathew, S. C.; Biju, A. Tetrahedron Lett. 2007, 48, 9018
18. Tomizawa, T.; Orimoto, K.; Niwa, T. Org. Lett. 2012, 14, 6294
19. Wyatt, P.; Anslow, A.; Coomber, B. Nucleosides Nucleot Nucl. 1995, 14, 2039
20. Li, Z.; Wu, Z.; Luo, F. J. Agr. Food Chem. 2005, 53, 3872
21. Speziale, A.; Smith, L. R.; Fedder, J. E. J. Org. Chem. 1965, 30, 4306
22. Speziale, A.; Smith, L. J. Org. Chem. 1963, 28, 1805
23. Nuridzhanyan, K. Russ. Chem. Rev. 1970, 39, 130
24. Nowick, J. S.; Holmes, D. L.; Noronha, G. J. Org. Chem. 1996, 61, 3929
25. Barrett, A. G.; Betts, M. J.; Fenwick, A. J. Org. Chem. 1985, 50, 169
26. Saunders, J.; Slocombe, R. Chem. Rev. 1948, 43, 203
27. Arnold, R.; Nelson, J.; Verbanc, J. Chem. Rev. 1957, 57, 47
28. Tsuge, O.; Itoh, T.; Tashiro, M. Tetrahedron 1968, 24, 2583
29. Tsuge, O.; Sakai, K. Bull. Chem. Soc. Jpn. 1972, 45, 1534
30. Tlumak, R. L.; Day, J. C.; Slanga, J. P. J. Am. Chem. Soc. 1982, 104, 7257
31. Deng, M.-Z.; Caubere, P.; Senet, J. Tetrahedron 1988, 44, 6079
32. Wu, X. F.; Anbarasan, P.; Neumann, H. Angew. Chem., Int. Ed. 2010, 49, 9047
33. Wu, X.-F.; Neumann, H.; Beller, M. Chem. Soc. Rev. 2011, 40, 4986
34. Wu, X.-F.; Neumann, H.; Beller, M. Chem. Rev. 2012, 113, 1
35. Wu, X. F.; Anbarasan, P.; Neumann, H. Angew. Chem., Int. Ed 2010, 49, 7316
36. Tsuji, J.; Chemiker, J.; Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons: Chichester, U.K., 1995.
37. Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; John Wiley & Sons: 2006.
38. Bjerglund, K.; Lindhardt, A. T.; Skrydstrup, T. J. Org. Chem. 2012, 77, 3793
39. Korsager, S.; Nielsen, D. U.; Taaning, R. H. Angew. Chem., Int. Ed. 2013, 125, 9945
40. Burhardt, M. N.; Taaning, R. H.; Skrydstrup, T. Org. Lett. 2013, 15, 948
41. Neumann, K. T.; Lindhardt, A. T.; Skrydstrup, T. Org. Lett. 2014, 16, 2216
42. Vinogradova, E. V.; Park, N. H.; Buchwald, S. L. Org. Lett. 2013, 15, 1394
43. Vinogradova, E. V.; Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 11132
44. Kianmehr, E.; Baghersad, M. H. Adv. Synth. Catal. 2011, 353, 2599
45. Yin, H.; Chen, B.; Ma, D. Tetrahedron 2013, 69, 5326
46. Yang, X.; Zhang, Y.; Ma, D. Adv. Synth. Catal. 2012, 354, 2443
47. Hermange, P.; Lindhardt, A. T.; Skrydstrup, T. J. Am. Chem. Soc. 2011, 133, 6061
48. Friis, S. D.; Skrydstrup, T.; Buchwald, S. L. Org. Lett. 2014, 16, 4296
49. Tanaka, K. I.; Yoshifuji, S.; Nitta, Y. Chem. Pharm. Bull. 1988, 36, 3125
50. Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 5816
51. Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9330
52. Culkin, D. A.; Hartwig, J. F. Organometallics 2004, 23, 339