Highly chemoselective Pd-C catalytic hydrodechlorination leading to the highly efficient N-debenzylation of benzylamines

Journal of Organic Chemistry

Volumn 74, Issue 15, 2009, Pages 5671-5674

  Cheng, Chuanjie ^a   Sun, Jianwei ^a   Xing, Lixin ^a   Xu, Jimin ^a   Wang, Xinyan ^a   Hu, Yuefei ^a  

^a Tsinghua University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLAMINES; CATALYTIC HYDRODECHLORINATION; CATALYTIC SYSTEM; CHEMOSELECTIVE; DEBENZYLATION; QUANTITATIVE YIELDS; TRICHLOROETHANE;

AMINES;

PALLADIUM;

BENZYLAMINE DERIVATIVE; CARBON; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEBENZYLATION; DECHLORINATION; HYDROGENOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

BENZYLAMINES; CARBON; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM; TRICHLOROETHANES;

EID: 68049111568     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9007282     Document Type: Article

References (44)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons, Inc.: New York, 1999.
2. For selected references, see: (a) Asahina, Y.; Takei, M.; Kimura, T.; Fukuda, Y. J. Med. Chem. 2008, 51, 3238-3249.
3. (b) Gonzlez-Sabn, J.; Gotor, V.; Rebolledo, F. J. Org. Chem. 2007, 72, 1309-1314.
4. (c) Faler, C. A.; Joulli, M. M. Org. Lett. 2007, 9, 1987-1990.
5. (d) Arefalk, A.; Larhed, M.; Hallberg, A. J. Org. Chem. 2005, 70, 938-942.
6. (e) White, K. N.; Konopelski, J. P. Org. Lett. 2005, 7, 4111-4112.
7. (f) Wang, X. J.; Hart, S. A.; Xu, B.; Mason, M. D.; Goodell, J. R.; Etzkorn, F. A. J. Org. Chem. 2003, 68, 2343-2349.
8. (g) Kuehne, M. E.; Cowen, S. D.; Xu, F.; Borman, L. J. Org. Chem. 2001, 66, 5303-5316.
9. (h) Liras, S.; Lynch, C. L.; Fryer, A. M.; Vu, B. T.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 5918-5924.
10. For selected references, see: (a) Resek, J. E. J. Org. Chem. 2008, 73, 9792-9794.
11. (b) Amat, M.; Perez, M.; Minaglia, A. T.; Bosch, J. J. Org. Chem. 2008, 73, 6920-6923.
12. (c) Santarem, M.; Vanucci-Bacque, C.; Lhommet, G. J. Org. Chem. 2008, 73, 6466-6469.
13. (d) Amat, M.; Griera, R.; Fabregat, R.; Molins, E.; Bosch, J. Angew. Chem., Int. Ed. 2008, 47, 3348-3351.
14. (e) Noel, R.; Vanucci-Bacqué, C.; Fargeau-Bellassoued, M.-C.; Lhommet, G. Eur. J. Org. Chem. 2007, 476-486.
15. (f ) Chi, Y.; English, E. P.; Pomerantz, W. C.; Seth Horne, W.; Joyce, L. A.; Alexander, L. R.; Fleming, W. S.; Hopkins, E. A.; Gellman, S. H. J. Am. Chem. Soc. 2007, 129, 6050-6055.
16. (g) Amat, M.; Bassas, O.; Llor, N.; Cantl, M.; Prez, M.; Molins, E.; Bosch, J. Chem. - Eur. J. 2006, 12, 7872-7881.
17. (h) Fujita, K.-i.; Fujii, T.; Yamaguchi, R. Org. Lett. 2004, 6, 3525-3528.
18. (i) Bunnage, M. E.; Davies, S. D.; Roberts, P. M.; Smith, A. D.; Withey, J. M. Org. Biomol. Chem. 2004, 2, 2763-2776.
19. Wang, X.; Dong, Y.; Sun, J.; Xu, X.; Li, R.; Hu, Y. J. Org. Chem. 2005, 70, 1897-1900.
20. For amine products with small molecular weights, see: (a) Evans, G. B.; Furneaux, R. H.; Greatrex, B.; Murkin, A. S.; Schramm, V. L.; Tyler, P. C. J. Med. Chem. 2008, 51, 948-956.
21. (b) Davies, S. G.; Garner, A. C.; Goddard, E. C.; Kruchinin, D.; Roberts, P. M.; Rodriguez-Solla, H.; Smith, A. D. Chem. Commun. 2006, 2664-2666.
22. (c) Kaur, K.; Aeron, S.; Bruhaspathy, M.; Shetty, S. J.; Gupta, S.; Hegde, L. H.; Silamkoti, A. D. V.; Mehta, A.; Chugh, A.; Gupta, J. B.; Sarmaa, P. K. S.; Kumara, N. Bioorg. Med. Chem. Lett. 2005, 15, 2093-2096.
23. (d) Hulin, B.; Cabral, S.; Lopaze, M. G.; Van Volkenburg, M. A.; Andrews, K. M.; Parker, J. C. Bioorg. Med. Chem. Lett. 2005, 15, 4770-4773.
24. For amine products with multihydrophilic groups, see: (a) Pandey, G.; Bharadwaj, K. C.; Khan, M. I.; Shashidhara, K. S.; Puranik, V. G. Org. Biomol. Chem. 2008, 6, 2587-2595.
25. (b) Carreño, M. C.; Hernández-Torres, G.; Urbano, A.; Colobert, F. Eur. J. Org. Chem. 2008, 2035-2038.
26. (c) Gelmi, M. L.; Cattaneo, C.; Pellegrino, S.; Clerici, F.; Montali, M.; Martini, C. J. Org. Chem. 2007, 72, 9811-9814.
27. (d) Galeazzi, R.; Martelli, G.; Mobbili, G.; Orena, M.; Rinaldi, S. Tetrahedron: Asymmetry 2004, 15, 3249-3256.
28. (e) Pandey, G.; Kapur, M. Org. Lett. 2002, 4, 3883-3886.
29. (f) Mehta, G.; Lakshminath, S. Tetrahedron Lett. 2002, 43, 331-334.
30. (g) Amat, M.; Llor, N.; Huguet, M.; Molins, E.; Espinosa, E.; Bosch, J. Org. Lett. 2001, 3, 3257-3260.
31. (a) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2002, 102, 4009-4092.
32. (b) Nishimura, S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis; John Wiley & Sons, Inc.: New York, 2001; pp 623-639.
33. (c) Rylander, P. N. Hydrogenation Methods; Academic Press: London, 1985; pp 148-156.
34. (a) Xia, C.; Liu, Y.; Xu, J.; Yu, J.; Qin, W.; Liang, X. Catal. Commun. 2009, 10, 456-458.
35. (b) Kume, A.; Monguchi, Y.; Hattori, K.; Nagase, H.; Sajiki, H. Appl. Catal., B 2008, 81, 274-282.
36. (c) Concibido, N. C.; Okuda, T.; NaKano, Y.; Nishijima, W.; Okada, M. Tetrahedron Lett. 2005, 46, 3613-3617.
37. (d) Nishijima, W.; Ochi, Y.; Tsai, T. Y.; Nakano, Y.; Okada,M. Appl. Catal., B 2004, 51, 135-140.
38. Prati, L.; Rossi, M. Appl. Catal., B 1999, 23, 135-142.
39. Because HCl molecules occupy the Pd-C catalytic sites unreversably under anhydrous conditions (anhydrous HCl is a strong poison for Pd-C catalyst) and its amount is not easily controllable, anhydrous gaseous HCl could not be used for this purpose. See : Nishimura, S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis; John Wiley & Sons, Inc.: New York, 2001; Chapter 2.
40. Details are described in Supporting Information.
41. For selected references, see (a) Tircsó, G.; Bényei, A.; Király, R.; Lázár, I.; Pál, R.; Brücher, E. Eur. J. Inorg. Chem. 2007, 701-713.
42. (b) Lee, J.-D.; Lee, Y. J.; Jeong, H.-J.; Lee, J. S.; Lee, C. H.; Ko, J.; Kang, S. O. Organometallics 2003, 22, 445-449.
43. (c) Kuehne, M. E.; Cowen, S. D.; Xu, F.; Borman, L. S. J. Org. Chem. 2001, 66, 5303-5316.
44. (d) Studer, M.; Blaser, H.-U. J. Mol. Catal. A: Chem. 1996, 112, 437-445.