Lewis base catalysis by thiourea: N -bromosuccinimide-mediated oxidation of alcohols

Journal of Organic Chemistry

Volumn 77, Issue 3, 2012, Pages 1592-1598

  Tripathi, Chandra Bhushan ^a   Mukherjee, Santanu ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOSELECTIVE OXIDATION; LEWIS BASE; MILD REACTION CONDITIONS; ORGANOCATALYSTS; OXIDATION OF ALCOHOLS; PRIMARY ALCOHOLS; SECONDARY ALCOHOLS; SMALL MOLECULES; THIOUREA DERIVATIVES; UREA DERIVATIVES;

CATALYSIS; HYDROGEN BONDS; THIOUREAS;

OXIDATION;

1,3 BIS (4 METHOXYPHENYL)THIOUREA; 1,3 BIS[3,5 BIS(TRIFLUOROMETHYL)PHENYL] 1,3 DIMETHYLTHIOUREA; 1,3 BIS[3,5 BIS(TRIFLUOROMETHYL)PHENYL]THIOUREA; ALCOHOL; CYCLOHEXYL [3,5 BIS(TRIFLUOROMETHYL)PHENYL]CARBAMATE; LEWIS BASE; N BROMOSUCCINIMIDE; N CYCLOHEXYL N' [3,5 BIS(TRIFLUOROMETHYL)PHENYL]THIOUREA; N CYCLOHEXYL N' [3,5 BIS(TRIFLUOROMETHYL)PHENYL]UREA; N,N' DIMETHYL N,N' DIPHENYLTHIOUREA; O PHENYL N METHYL N PHENYLTHIOCARBAMATE; THIOCARBANILIDE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; HYDROGEN BOND;

EID: 84856660154     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202269p     Document Type: Article

References (49)

1. Asymmetric Organocatalysis; Berkessel, A. and Gröger, H., Eds.; Wiley-VCH: Weinheim, 2005.
2. Enantioselective Organocatalysis; Dalko, P. I., Ed.;: Weinheim, 2007.
3. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175
4. Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719-724
5. Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217-220
6. Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012-10014
7. Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299-4306
8. Connon, S. J. Chem.-Eur. J. 2006, 12, 5418-5427
9. Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520-1543
10. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713-5743
11. Zhang, Z.; Schreiner, P. R. Chem. Soc. Rev. 2009, 38, 1187-1198
12. Taylor, M. S.; Tokunaga, N.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 6700-6704
13. Pan, S. C.; Zhou, J.; List, B. Angew. Chem., Int. Ed. 2007, 46, 612-614
14. Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404-13405
15. Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 7198-7199
16. Peterson, E. A.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2009, 48, 6328-6331
17. Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193-4195
18. Lacour, J.; Moraleda, D. Chem. Commun. 2009, 7073-7089
19. Xu, H.; Zuend, S. J.; Woll, M. P.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986-990
20. Knowles, R. R.; Lin, S.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 5030-5032
21. Brown, A. R.; Kuo, W.-H.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 9286-9288
22. De, C. K.; Klauber, E. G.; Seidel, D. J. Am. Chem. Soc. 2009, 131, 17060-17061
23. Birrell, J. A.; Desrosiers, J.-N.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 13872-13875
24. De, C. K.; Seidel, D. J. Am. Chem. Soc. 2011, 133, 14538-14541
25. Burns, N. Z.; Witten, M. R.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 14578-14581
26. Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289-296
27. Zuend, S. J.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 15872-15883
28. Zuend, S. J.; Jacobsen, E. N. J. Am. Chem. Soc. 2009, 131, 15358-15374
29. Etzenbach-Effers, K.; Berkessel, A. Top. Curr. Chem. 2010, 291, 1-27
30. Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560-1638
31. Gawronski, J.; Wascinska, N.; Gajewy, J. Chem. Rev. 2008, 108, 5227-5252
32. Denmark, S. E.; Burk, M. T. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20655-20660
33. Metrangolo, P.; Resnati, G. Chem.-Eur. J. 2001, 7, 2511-2519
34. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386-395
35. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Angew. Chem., Int. Ed. 2008, 47, 6114-6127
36. Arman, H. D.; Gieseking, R. L.; Hanks, T. W.; Pennington, W. T. Chem. Commun. 2010, 46, 1854-1856
37. Veitch, G. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 7332-7335
38. Zhou, L.; Tan, C. K.; Jiang, X.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 15474-15476
39. Zhou, L.; Chen, J.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2011, 133, 9164-9167
40. Tan, C. K.; Zhou, L.; Yeung, Y.-Y. Synlett 2011, 1335-1339
41. Feiser, L. F.; Rajagopalan, S. J. Am. Chem. Soc. 1949, 71, 3935-3938
42. Feiser, L. F.; Rajagopalan, S. J. Am. Chem. Soc. 1949, 71, 3938-3941
43. Kruse, P. F., Jr.; Geurkink, N.; Grist, K. L. J. Am. Chem. Soc. 1954, 76, 5796-5797
44. Stuckwisch, C. G.; Hammer, G. G.; Blau, N. F. J. Org. Chem. 1957, 22, 1678-1680
45. Fan, J.-C.; Shang, Z.-C.; Liang, J.; Liu, X.-H.; Liu, Y. J. Phy. Org. Chem. 2008, 21, 945-953
46. Kim, K. S.; Cho, I. H.; Yoo, B. K.; Song, Y. H.; Hahn, C. S. J. Chem. Soc., Chem. Commun. 1984, 762-763
47. Kuhakarn, C.; Kittigowittana, K.; Pohmakotr, M.; Reutrakul, V. Tetrahedron 2005, 61, 8995-9000
48. Arterburn, J. B. Tetrahedron 2001, 57, 9765-9788
49. Tojo, G.; Fernandez, M. I. In Oxidation of Alcohols to Aldehydes and Ketones: A Guide to Current Common Practice; Springer: New York, 2006; Chapter 10, pp 339-349.