Iron-catalyzed C-C bond formation at α-position of aliphatic amines via C-H bond activation through 1,5-hydrogen transfer

Journal of the American Chemical Society

Volumn 132, Issue 16, 2010, Pages 5568-5569

  Yoshikai, Naohiko ^a,b   Mieczkowski, Adam ^a   Matsumoto, Arimasa ^a   Ilies, Laurean ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC AMINES; ALKENYLATION; AMINE GROUPS; ARYLATIONS; C-C BOND FORMATION; C-H BOND; CATALYTIC AMOUNTS; CH-BOND ACTIVATION; DIORGANOZINC REAGENTS; GRIGNARD; HYDROGEN TRANSFER; MECHANISTIC STUDIES;

CHEMICAL BONDS; HYDROCARBONS;

REACTION KINETICS;

ALIPHATIC AMINE; GRIGNARD REAGENT; HYDROGEN; IRON; PYRROLIDINE DERIVATIVE;

ALKYLATION; ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; DIMERIZATION; HYDROGEN BOND; REDUCTION; STEREOCHEMISTRY;

EID: 77952568253     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja100651t     Document Type: Article

References (30)

1. Iron Catalysis in Organic Chemistry; Plietker, B., Ed.; Wiley-VCH: Weinheim, 2008.
2. Bolm, C., Legros, J., Le Paih, J., and Zani, L. Chem. Rev. 2004, 104, 6217-6254
3. Enthaler, S., Junge, K., and Beller, M. Angew. Chem., Int. Ed. 2008, 47, 3317-3321
4. Sherry, B. D. and Fürstner, A. Acc. Chem. Res. 2008, 41, 1500-1511
5. Nakamura, M., Hirai, A., and Nakamura, E. J. Am. Chem. Soc. 2000, 122, 978-979
6. Nakamura, M., Matsuo, K., Inoue, T., and Nakamura, E. Org. Lett. 2003, 5, 1373-1375
7. Nakamura, M., Matsuo, K., Ito, S., and Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686-3687
8. Nakamura, M., Ito, S., Matsuo, K., and Nakamura, E. Synlett 2005, 1794-1798
9. Norinder, J., Matsumoto, A., Yoshikai, N., and Nakamura, E. J. Am. Chem. Soc. 2008, 130, 5858-5859
10. Yoshikai, N., Matsumoto, A., Norinder, J., and Nakamura, E. Angew. Chem., Int. Ed. 2009, 48, 2975-2978
11. Yoshikai, N., Matsumoto, A., Norinder, J., and Nakamura, E. Synlett 2010, 313-316
12. 3 C-H bond activation
13. Godula, K. and Sames, D. Science 2006, 312, 67-72
14. Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, 2005.
15. Kakiuchi, F. and Chatani, N. Adv. Synth. Catal. 2003, 345, 1077
16. Chen, X., Engle, K. M., Wang, D.-H., and Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094-5115
17. Snieckus, V., Cuevas, J.-C., Sloan, C. P., Liu, H., and Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896-898
18. Williams, L., Booth, S. E., and Undheim, K. Tetrahedron 1994, 50, 13697-13708
19. Robertson, M., Peplow, M. A., and Pillai, J. Tetrahedron Lett. 1996, 37, 5825-5828
20. Murakami, M., Hayashi, M., and Ito, Y. Appl. Organomet. Chem. 1995, 9, 385-397
21. Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069-1084 references therein
22. Arylation with boron reagents
23. Pastine, S. J., Gribkov, D. V., and Sames, D. J. Am. Chem. Soc. 2006, 128, 14220-14221
24. Basle, O. and Li, C.-J. Org. Lett. 2008, 10, 3661-3663
25. Inoue, A., Shinokubo, H., and Oshima, K. Synlett 1999, 1582-1584
26. Tsou, T. T. and Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319-6332
27. 2Zn reagent gave a much poorer yield of the phenylation products than PhMgBr.
28. Fürstner, A., Martin, R., Krause, H., Seidel, G., Goddard, R., and Lehmann, C. W. J. Am. Chem. Soc. 2008, 130, 8773-8787
29. Noda, D., Sunada, Y., Hatakeyama, T., Nakamura, M., and Nagashima, H. J. Am. Chem. Soc. 2009, 131, 6078-6079
30. Vallée, F., Mousseau, J. J., and Charette, A. B. J. Am. Chem. Soc. 2010, 132, 1514-1516