Iridium-catalyzed condensation of primary amines to form secondary amines

Synthesis

Volumn , Issue 24, 2009, Pages 4110-4112

  Lorentz Petersen, Linda L R ^a   Jensen, Paw ^a   Madsen, Robert ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

Amines; Dimerizations; Homogeneous catalysis; Hydrogen transfer; Iridium

Indexed keywords

DIMERIZATIONS; GOOD YIELD; HOMOGENEOUS CATALYSIS; HYDROGEN TRANSFER; PENTAMETHYLCYCLOPENTADIENYL; PRIMARY AMINES; SECONDARY AMINES;

CATALYSIS; DIMERIZATION; DISTILLATION; HYDROGEN; IRIDIUM; REACTION KINETICS;

AMINES;

AMINE; BIS(4 BROMOBENZYL)AMINE; BIS(4 CHLOROBENZYL)AMINE; BIS(4 FLUOROBENZYL)AMINE; BIS(4 METHOXYBENZYL)AMINE; BIS(4 METHYLBENZYL)AMINE; BIS[(2 PYRIDYL)METHYL]AMINE; DIBENZYLAMINE; DICYCLOHEXYLAMINE; DIHEXYLAMINE; DIOCTYLAMINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; DEHYDROGENATION; DIMERIZATION; GAS CHROMATOGRAPHY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 78650750527     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217058     Document Type: Article

References (38)

1. (a) Lawrence, S. A. Amines: Synthesis, Properties and Applications; Cambridge University Press: Cambridge 2004.
2. (b) Salvatore, R. N.; Yoon, C. H.; Jung, K. W. Tetrahedron 2001, 57, 7785.
3. (a) Singh, C. B.; Kavala, V.; Samal, A. K.; Patel, B. K. Eur. J. Org. Chem. 2007, 1369.
4. (b) Salvatore, R. N.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2002, 67, 674.
5. (a) Tripathi, R. P.; Verma, S. S.; Pandey, J.; Tiwari, V. K. Curr. Org. Chem. 2008, 12, 1093.
6. (b) Abdel-Magid, A. F.; Mehrman, S. J. Org. Process Res. Dev. 2006, 10, 971.
7. Kan, T.; Fukuyama, T. Chem. Commun. 2004, 353.
8. (a) Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534.
9. (b) Surry, D. S.; Buchwald, S. L. Angew. Chem. Int. Ed. 2008, 47, 6338.
10. (a) Nacario, R.; Kotakonda, S.; Fouchard, D. M. D.; Tillekeratne, L. M. V.; Hudson, R. A. Org. Lett. 2005, 7, 471.
11. (b) Sajiki, H.; Ikawa, T.; Hirota, K. Org. Lett. 2004, 6, 4977.
12. (a) Núnez Magro, A. A.; Eastham, G. R.; Cole-Hamilton, D. J. Chem. Commun. 2007, 3154.
13. (b) Hanada, S.; Ishida, T.; Motoyama, Y.; Nagashima, H. J. Org. Chem. 2007, 72, 7551.
14. (a) Blank, B.; Michlik, S.; Kempe, R. Chem. Eur. J. 2009, 15, 3790.
15. (b) Hamid, M. H. S. A.; Allen, C. L.; Lamb, G. W.; Maxwell, A. C.; Maytum, H. C.; Watson, A. J. A.; Williams, J. M. J. J. Am. Chem. Soc. 2009, 131, 1766.
16. (c) Fujita, K.-i.; Enoki, Y.; Yamaguchi, R. Tetrahedron 2008, 64, 1943.
17. (d) Yamaguchi, R.; Kawagoe, S.; Asai, C.; Fujita, K.-i. Org. Lett. 2008, 10, 181.
18. (e) Hollmann, D.; Tillack, A.; Michalik, D.; Jackstell, R.; Beller, M. Chem. Asian J. 2007, 2, 403.
19. (a) Prades, A.; Corberán, R.; Poyatos, M.; Peris, E. Chem. Eur. J. 2008, 14, 11474.
20. (b) Hollmann, D.; Bähn, S.; Tillack, A.; Beller, M. Chem. Commun. 2008, 3199.
21. (c) Bähn, S.; Hollmann, D.; Tillack, A.; Beller, M. Adv. Synth. Catal. 2008, 350, 2099
22. (d) Hollmann, D.; Bähn, S.; Tillack, A.; Beller, M. Angew. Chem. Int. Ed. 2007, 46, 8291
23. With Pt/C and Al, see: (a) Miyazawa, A.; Saitou, K.; Tanaka, K.; Gädda, T. M.; Tashiro, M.; Prakash, G. K. S.; Olah, G. A. Tetrahedron Lett. 2006, 47, 1437
24. 2O, see: (b) Tsuji, Y.; Shida, J.; Takeuchi, R.; Watanabe, Y. Chem. Lett. 1984, 889
25. With Pd/C, see: (c) Murahashi, S.-I.; Yoshimura, N.; Tsumiyama, T.; Kojima, T. J. Am. Chem. Soc. 1983, 105, 5002
26. 3, see: (d) Khai, B. T.; Concilio, C.; Porzi, G. J. Organomet. Chem. 1981, 208, 249.
27. With Raney nickel, see: (e) De Angelis, F.; Grgurina, I.; Nicoletti, R Synthesis 1979, 70.
28. Largeron, M.; Fleury, M.-B. Org. Lett. 2009, 11, 883.
29. Nordstrøm, L. U.; Madsen, R. Chem. Commun. 2007, 5034.
30. Katritzky, A. R.; Zhao, X.; Hitchings, G. J. Synthesis 1991, 703.
31. Juday, R.; Adkins, H. J. Am. Chem. Soc. 1955, 77, 4559
32. Anastasi, C.; Hantz, O.; De Clercq, E.; Pannecouque, C.; Clayette, P.; Dereuddre-Bosquet, N.; Dormont, D.; Gondois-Rey, F.; Hirsch, I.; Krau, J.-L. J. Med. Chem. 2004, 47, 1183.
33. Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192.
34. Braun, J. V.; Kühn, M.; Weismantel, J. Leibigs Ann. Chem. 1926, 449, 249.
35. Incarvito, C.; Lam, M.; Rhatigan, B.; Rheingold, A. L.; Qin, C. J.; Gavrilova, A. L.; Bosnich, B. J. Chem. Soc., Dalton Trans. 2001, 3478.
36. Eggert, H.; Djerassi, C. J. Am. Chem. Soc. 1973, 95, 3710.
37. Closson, R. D.; Napolitano, J. P.; Ecke, G. G.; Kolka, A. J. J. Org. Chem. 1957, 22, 646.
38. Miller, R. E. J. Org. Chem. 1960, 25, 2126.