A biomimetic electrocatalytic system for the atom-economical chemoselective synthesis of secondary amines

Organic Letters

Volumn 11, Issue 4, 2009, Pages 883-886

  Largeron, Martine ^a   Fleury, M B ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMMONIA; BIOMIMETIC MATERIAL; IMINE;

ARTICLE; BIOMIMETICS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

AMINES; AMMONIA; BIOMIMETIC MATERIALS; BIOMIMETICS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; IMINES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 62749181843     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802885b     Document Type: Article

References (35)

1. For a review on the synthesis of secondary amines, see: Salvatore, R. N.; Yoon, C. H.; Jung, K. W. Tetrahedron 2001, 57, 7785-7811.
2. For recent reviews on catalytic hydroamination of alkynes and alkenes, see: (a) Severin, R.; Doye, S. Chem. Soc. Rev. 2007, 36, 1407-1420.
3. (b) Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795-3892.
4. For recent reviews on met al.-catalyzed amination of aryl halides, see: (a) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338-6361.
5. (b) Hartwig, J. F. Nature 2008, 455, 314-322.
6. (c) Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534-1544.
7. For selected recent examples see: (a) Fujita, K.-I.; Yamaguchi, R. Synlett., 2005, 4, 560-571.
8. (b) Tillack, D.; Hollmann, D.; Michalik, R.; Jackstell, R.; Beller, M. Tetrahedron Lett. 2006, 47, 8881-8885.
9. (c) Hoolman, D.; Tillack, A.; Michalik, D.; Jackstell, R.; Beller, M. Chem. Asian J. 2007, 2, 403-410.
10. (d) Hamid, M. H. S. A.; Williams, M. J. Chem. Commun. 2007, 725-727.
11. (e) Nordstrom, L. U.; Madsen, R. Chem. Commun. 2007, 5034-5036.
12. (f) Fujita, K.-I.; Enoki, Y.; Yamaguchi, R. Tetrahedron 2008, 64, 1943-1954.
13. (g) Yamaguchi, R.; Kawagoe, S.; Asai, C.; Fujita, K.-I. Org. Lett. 2008, 10, 181-184.
14. (h) Pontes da Costa, A.; Viciano, M.; Sanau, M.; Merino, S.; Tejeda, J.; Peris, E.; Royo, B. Organomet al.lics 2008, 27, 1305-1309.
15. (a) Hollmann, D.; Bähn, S.; Tillack, A.; Beller, M. Angew. Chem., Int. Ed. 2007, 46, 8291-8294.
16. (b) Hollmann, D.; Bähn, S.; Tillack, A.; Beller, M. Chem. Commun. 2008, 3199-3201.
17. (c) Hollmann, D.; Bähn, S.; Tillack, A.; Parton, R.; Altink, R.; Beller, M. Tetrahedron Lett. 2008, 49, 5742-5745.
18. Sajiki, H.; Ikawa, T.; Hirota, K. Org. Lett. 2004, 6, 4977-4980.
19. (a) Blackburn, L.; Taylor, R. J. K. Org. Lett. 2001, 3, 1637-1639.
20. (b) Kanno, H.; Taylor, R. J. K. Tetrahedron Lett. 2002, 43, 7337-7340.
21. (c) Taylor, R. J. K.; Reid, M.; Foot, J.; Raw, S. A. Acc. Chem. Res. 2005, 38, 851-869.
22. For recent papers, see: (a) Adenier, A.; Chehimi, M. M.; Gallardo, I.; Pinson, J.; Vilà, N. Langmuir 2004, 20, 8243-8253.
23. (b) Gallardo, I.; Pinson, J.; Vilà, N. J. Phys. Chem. B 2006, 110, 19521-19529.
24. (c) Bourdelande, J. L.; Gallardo, I.; Guirado, G. J. Am. Chem. Soc. 2007, 129, 2817-2821.
25. (a) Largeron, M.; Neudörffer, A.; Fleury, M.-B. Angew. Chem., Int. Ed. 2003, 42, 1026-1029.
26. (b) Largeron, M.; Chiaroni, A.; Fleury, M.-B. Chem.-Eur. J. 2008, 14, 996-1003.
27. (a) Largeron, M.; Neudörffer, A.; Vuilhorgne, M.; Blattes, E.; Fleury, M.-B. Angew. Chem., Int. Ed. 2002, 41, 824-827.
28. (b) Blattes, E.; Fleury, M.-B.; Largeron, M. J. Org. Chem. 2004, 69, 882-890.
29. (c) Blattes, E.; Lockhart, B.; Lestage, P.; Schwendimann, L.; Gressens, P.; Fleury, M.-B.; Largeron, M. J. Med. Chem. 2005, 48, 1282-1286.
30. (d) Xu, D.; Chiaroni, A.; Fleury, M.-B.; Largeron, M. J. Org. Chem. 2006, 71, 6374-6381.
31. The formation of related diamines has already been observed from the one-electron cathodic reduction of aldimines. See, for example: (a) Tanaka, H.; Nakahara, T.; Dhimane, H.; Torii, S. Synlett 1989, 51-52.
32. (b) Largeron, M.; Fleury, M.-B. J. Org. Chem. 2000, 65, 8874-8881.
33. (c) Siu, T.; Li, W.; Yudin, A. K. J. Comb. Chem. 2001, 3, 554-558.
34. (a) Togrul, M.; Turgut, Y.; Hosgoren, H. Chirality 2004, 16, 351-355.
35. (b) Togrul, M.; Askin, M.; Hosgoren, H. Tetrahedron: Asymmetry 2005, 16, 2771-2777.