Heterogeneous catalytic hydrogenation of unprotected indoles in water: A green solution to a long-standing challenge

Organic Letters

Volumn 13, Issue 19, 2011, Pages 5124-5127

  Kulkarni, Aditya ^a   Zhou, Weihong ^a   Török, Béla ^a  

^a UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4-TOLUENESULFONIC ACID; BENZENESULFONIC ACID DERIVATIVE; INDOLE DERIVATIVE; SOLVENT; TOLUENESULFONIC ACID; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION;

BENZENESULFONATES; CATALYSIS; HYDROGENATION; INDOLES; MOLECULAR STRUCTURE; SOLVENTS; WATER;

EID: 80054773639     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2019899     Document Type: Article

References (33)

1. Bird, C. W. Tetrahedron 1992, 48, 335.
2. Maxted, E. B.; Biggs, M. S. J. Chem. Soc. 1957, 3844.
3. Nishimura, S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis; Wiley: New York, 2001.
4. Zhou, Y. G. Acc. Chem. Res. 2007, 40, 1357.
5. Gribble, G. W.; Lord, P. D.; Skotnicki, J.; Dietz, S. E.; Eaton, J. T.; Johnson, J. J. Am. Chem. Soc. 1974, 96, 7812.
6. Gribble, G. W.; Hoffman, J. H. Synthesis 1977, 859.
7. Berger, J. G. Synthesis 1974, 508.
8. Lanzilotti, A. E.; Littell, R.; Fanshawe, W. J.; McKenzie, T. C.; Lovell, F. M. J. Org. Chem. 1979, 44, 4809.
9. Tan, M.; Zhang, Y. Tetrahedron Lett. 2009, 50, 4912.
10. Robinson, B. Chem. Rev. 1969, 69, 785.
11. Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614.
12. Kuwano, R.; Kaneda, K.; Ito, T.; Sato, K.; Kurokawa, T.; Ito, T. Org. Lett. 2004, 6, 2213.
13. Kuwano, R.; Kashiwabara, M. Org. Lett. 2006, 8, 2653.
14. Baeza, A.; Pfaltz, A. Chem.;Eur. J. 2010, 16, 2036.
15. Horvath, I., Ed. Encyclopedia of Catalysis; Wiley: New York, 2003.
16. Kulkarni, A.; Török, B. Curr. Org. Synth. 2011, 8, 187.
17. Gilchrist, T. L.; Graham, K. Tetrahedron 1997, 53, 791.
18. Chandrasekhar, S.; Basu, D.; Reddy, C. R. Synthesis 2007, 1509.
19. Shaw, J. E.; Stapp, P. R. J. Heterocycl. Chem. 1987, 24, 1477.
20. Chen, C. B.; Wang, X. F.; Cao, Y. J.; Cheng, H. G.; Xiao, W. J. J. Org. Chem. 2009, 74, 3532.
21. Gilchrist, T. L. Heterocyclic Chemistry, 3rd ed.; Pearson: Essex, 1997; p 240.
22. Wang, D. S.; Chen, Q. A.; Li, W.; Yu, C. B.; Zhou, Y. G.; Zhang, X. J. Am. Chem. Soc. 2010, 132, 8909.
23. Wang, D. S.; Tang, J.; Zhou, Y. G.; Chen, M. W.; Yu, C. B.; Duan, Y.; Jiang, G. F. Chem. Sci. 2011, 2, 803.
24. Ishii, H.; Murakami, K.; Sakurada, E.; Hosoya, K.; Murakami, Y. J. Chem. Soc., Perkin Trans. 1 1988, 2377.
25. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M; Goldberg, J. A. Chem. Rev. 1997, 97, 787.
26. Dounay, Z. A. B.; Overman, L. E.; Wrobleski, A. D. J. Am. Chem. Soc. 2005, 127, 10186.
27. Natesh, R.; Schwager, S. L. U.; Evans, H. R.; Sturrock, E. D.; Acharya, K. R. Biochemistry 2004, 43, 8718.
28. Gruenfeld, N.; Stanton, J. L.; Yuan, A. M.; Ebetino, F. H.; Browne, J. J.; Gude, C.; Huebner, C. F. J. Med. Chem. 1983, 26, 1277.
29. Anas, S.; Kagan, H. B. Tetrahedron: Asymmetry 2009, 20, 2193.
30. Liu, D.; Zhao, G.; Xiang, L. Eur. J. Org. Chem. 2010, 3975.
31. Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163.
32. See the Supporting Information for details.
33. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, 1998.