PdCl2 catalyzed efficient assembly of organic azides, CO, and alcohols under mild conditions: A direct approach to synthesize carbamates

Chemical Communications

Volumn 50, Issue 28, 2014, Pages 3706-3709

  Ren, Long ^a   Jiao, Ning ^a,b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AZIDE; CARBAMIC ACID DERIVATIVE; CARBON MONOXIDE; ISOCYANIC ACID DERIVATIVE; PALLADIUM; PALLADIUM CHLORIDE; CARBAMIC ACID; ISOCYANATE; LEAD CHLORIDE; MACROCYCLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS; ATMOSPHERE; CATALYST; CHEMICAL STRUCTURE; MOLECULE; TEMPERATURE;

ALCOHOLS; AZIDES; CARBAMATES; CARBON MONOXIDE; CATALYSIS; ISOCYANATES; PALLADIUM;

EID: 84901743107     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc00538d     Document Type: Article

References (86)

1. E. Delebecq, J.-P. Pascault, B. Boutevin, F. Ganachaud, Chem. Rev., 2013, 113, 80
2. P. Braunstein, D. Nobel, Chem. Rev., 1989, 89, 1927
3. J. A. Varela, C. Saá, Chem. Rev., 2003, 103, 3787
4. R. K. Friedman, K. M. Oberg, D. M. Dalton, T. Rovis, Pure Appl. Chem., 2012, 82, 1353
5. A. D. Allen, T. T. Tidwell, Chem. Rev., 2013, 113, 7287
6. C. Wentrup, J. J. Finnerty, R. Koch, Curr. Org. Chem., 2011, 15, 1745
7. M.-W. Ding, G.-F. Yang, Trends Heterocycl. Chem., 2006, 11, 87
8. Z. Wang, S. M. Cohen, Chem. Soc. Rev., 2009, 38, 1315
9. D. Liu, K. Xia, R. Yang, Curr. Org. Chem., 2012, 16, 1838
10. K. V. Srinivasan, P. K. Chaskar, S. N. Dighe, D. S. Rane, P. V. Khade, K. S. Jain, Heterocycles, 2011, 83, 2451
11. T. Choshi, S. Hibino, Heterocycles, 2011, 83, 1205
12. P. Spanu, F. Ulgheri, Curr. Org. Chem., 2008, 12, 1071
13. J. H. Rigby, Synlett, 2000, 1
14. I. Gallou, Org. Prep. Proced. Int., 2007, 39, 55
15. J. H. Saunders, R. J. Slocombe, Chem. Rev., 1948, 43, 203
16. J. Weinstock, J. Org. Chem., 1961, 26, 3511
17. T. L. Capson, C. D. Poulter, Tetrahedron Lett., 1984, 25, 3515
18. H. Lebel, O. Leogane, Org. Lett., 2006, 8, 5717
19. Z.-H. Guan, H. Lei, M. Chen, Z.-H. Ren, Y. Bai, Y.-Y. Wang, Adv. Synth. Catal., 2012, 354, 489
20. B. Gabriele, R. Mancuso, G. Salerno, M. Costa, J. Org. Chem., 2003, 68, 601
21. E. V. Vinogradova, N. H. Park, B. P. Fors, S. L. Buchwald, Org. Lett., 2013, 15, 1394
22. X. Yang, Y. Zhang, D. Ma, Adv. Synth. Catal., 2012, 354, 2443
23. C. Mollar, C. R. de Arellano, M. Medio-Simón, G. Asensio, J. Org. Chem., 2012, 77, 9693
24. F. Ragaini, M. Gasperini, S. Cenini, L. Arnera, A. Caselli, P. Macchi, N. Casati, Chem.–Eur. J., 2009, 15, 8064
25. D. J. Díaz, A. K. Darko, L. McElwee-White, Eur. J. Org. Chem., 2007, 4453
26. Y. Zhang, M. Anderson, J. L. Weisman, M. Lu, C. J. Choy, V. A. Boyd, J. Price, M. Sigal, J. Clark, M. Connelly, F. Zhu, W. A. Guiguemde, C. Jeffries, L. Yang, A. Lemoff, A. P. Liou, T. R. Webb, J. L. DeRisi, R. K. Guy, ACS Med. Chem. Lett., 2010, 1, 460
27. J. In, S. Hwang, C. Kim, J. H. Seo, S. Kim, Eur. J. Org. Chem., 2013, 965
28. C. Ma, K. Jin, J. Cao, L. Zhang, X. Li, W. Xu, Bioorg. Med. Chem., 2013, 21, 1621
29. H. Lebel, O. Leogane, Org. Lett., 2005, 7, 4107
30. D. Milstein, Acc. Chem. Res., 1988, 21, 428
31. K. Khumtaveeporn, H. Alper, Acc. Chem. Res., 1995, 28, 414
32. R. Skoda-Foldes, L. Kollar, Curr. Org. Chem., 2002, 6, 1097
33. A. Brennführer, H. Neumann, M. Beller, Angew. Chem., Int. Ed., 2009, 48, 4114
34. R. P. Bennett, W. B. Hardy, J. Am. Chem. Soc., 1968, 90, 3295
35. G. L. La Monica, S. Cenini, J. Organomet. Chem., 1981, 216, C35
36. G. L. La Monica, G. Ardizzoia, J. Mol. Catal., 1986, 38, 327
37. H. Doi, J. Barletta, M. Suzuki, R. Noyori, Y. Watanabe, B. Långström, Org. Biomol. Chem., 2004, 2, 3063
38. N. Pendem, Y. R. Nelli, C. Douat, L. Fischer, M. Laguerre, E. Ennifar, B. Kauffmann, G. Guichard, Angew. Chem., Int. Ed., 2013, 52, 4147
39. K. M. Patil, R. J. Naik, M. Fernandes, M. Ganguli, V. A. Kumar, J. Am. Chem. Soc., 2012, 134, 7196
40. G. H. Jin, H. J. Lee, H. J. Gim, J.-H. Ryu, R. Jeon, Bioorg. Med. Chem. Lett., 2012, 22, 3301
41. A. L. Wolfe, K. K. Duncan, N. K. Parelkar, S. J. Weir, G. A. Vielhauer, D. L. Boger, J. Med. Chem., 2012, 55, 5878
42. R. C. Gupta, Toxicology of Organophosphate and Carbamate Compounds, Academic, St Louis, 1st edn, 2005
43. C. Timchalk, Biomonitoring of Pesticides: Pharmacokinetics of Organophosphorus and Carbamate Insecticides, in Anticholinesterase Pesticides: Metabolism, Neurotoxicity, and Epidemiology, ed. T. Satoh and R. C. Gupta, John Wiley and Sons, Inc., Hoboken, NJ, USA, 2011
44. S. A. Mahler, R. M. Borland, Am. J. Cardiol., 1990, 65, 11D
45. H. J. Mann, Clin. Pharmacol., 1990, 9, 842
46. A. Fitton, M. T. Buckley, Drugs, 1990, 40, 138
47. L. D. Anna, M. M. John, E. T. James, Drugs, 2008, 68, 607
48. E. S. Carl, G. Seden, K. Peter, Nature Rev. Drug Discovery, 2011, 10, 729
49. J. G. Martin, H. L. Charles, S. Raman, Epilepsia, 2012, 53, 412
50. D. Tikoo, M. Gupta, Int. J. Pharmacol. Clin. Sci., 2012, 1, 85
51. R. Konrad, J. L. Jarogniew, B. Barbara, C. Roman, J. C. Stanislaw, Ther. Clin. Risk Manage., 2012, 8, 7
52. J. C. Adkins, R. N. Brogden, Drugs, 1998, 55, 121
53. C. J. Dunn, K. L. Goa, Drugs, 2001, 61, 285
54. S. D. Anderson, Treat. Respir. Med., 2004, 3, 365
55. C. M. Bonuccelli, Clin. Exp. Allergy Rev., 2001, 1, 274
56. F. Claude, J. Veronique, Expert Rev. Anti-Infect. Ther., 2004, 2, 671
57. Y. R. Natella, Expert Opin. Drug Metab. Toxicol., 2010, 6, 95
58. S. M. Clarke, F. M. Mulcahy, HIV Med., 2000, 1, 15
59. E. Martínez, M. A. García-Viejo, J. L. Blanco, L. Bianchi, E. Buira, I. Conget, R. Casamitjana, J. Mallolas, J. M. Gatell, Clin. Infect. Dis., 2000, 31, 1266
60. J. E. Leffler, R. D. Temple, J. Am. Chem. Soc., 1967, 89, 5235
61. A. A. Izzo, E. Ernst, Drugs, 2009, 69, 1777
62. D. F. Marsh and L. Hill, US Pat., 2890985, 1959
63. G. Özhan, S. Özden, B. Alpertunga, J. Environ. Sci. Health, Part B, 2005, 40, 827
64. C. Lentza-Rizos, A. Balokas, J. Agric. Food Chem., 2001, 49, 710
65. P. Mueller, C. Baud, I. Naegeli, J. Phys. Org. Chem., 1998, 11, 597
66. M. M. Abu-Omar, C. E. Shields, N. Y. Edwards, R. A. Eikey, Angew. Chem., Int. Ed., 2005, 44, 6203
67. H. M. L. Davies, M. S. Long, Angew. Chem., Int. Ed., 2005, 44, 3518
68. N. P. Mankad, P. Müller, J. C. Peters, J. Am. Chem. Soc., 2010, 132, 4083
69. A. I. Nguyen, R. A. Zarkesh, D. C. Lacy, M. K. Thorson, A. F. Heyduk, Chem. Sci., 2011, 2, 166
70. A. F. Heyduk, R. A. Zarkesh, A. I. Nguyen, Inorg. Chem., 2011, 50, 9849
71. S. Wiese, M. J. B. Aguila, E. Kogut, T. H. Warren, Organometallics, 2013, 32, 2300
72. Q. Zhang, C. Wu, L. Zhou, J. Li, Organometallics, 2013, 32, 415
73. R. E. Cowley, N. A. Eckert, J. Elhaık, P. L. Holland, Chem. Commun., 2009, 1760
74. T. G. Driver, Org. Biomol. Chem., 2010, 8, 3831
75. J. F. Berry, Dalton Trans., 2012, 41, 700
76. Z. Qu, W. Shi, J. Wang, J. Org. Chem., 2001, 66, 8139
77. C. Peng, Y. Wang, J. Wang, J. Am. Chem. Soc., 2008, 130, 1566
78. F. Ye, X. Ma, Q. Xiao, H. Li, Y. Zhang, J. Wang, J. Am. Chem. Soc., 2012, 134, 5742
79. J. Barluenga, C. Valdés, Angew. Chem., Int. Ed., 2011, 50, 7486
80. Z. Shao, H. Zhang, Chem. Soc. Rev., 2012, 41, 560
81. Y. Zhang, J. Wang, Eur. J. Org. Chem., 2011, 1015
82. Q. Xiao, Y. Zhang, J. Wang, Acc. Chem. Res., 2013, 46, 236
83. Z. Zhang, Y. Liu, L. Ling, Y. Li, Y. Dong, M. Gong, X. Zhao, Y. Zhang, J. Wang, J. Am. Chem. Soc., 2011, 133, 4330
84. Z. Zhang, Y. Zhang, J. Wang, ACS Catal., 2011, 1, 1621
85. N. Asao, T. Nogami, K. Takahashi, Y. Yammamoto, J. Am. Chem. Soc., 2002, 124, 764
86. Y. Xiao, J. Zhang, Angew. Chem., Int. Ed., 2008, 47, 1903