Manganese-catalyzed cross-coupling reactions of aliphatic amines with aryl halides

Tetrahedron Letters

Volumn 51, Issue 30, 2010, Pages 3910-3912

  Yong, Fui Fong ^a   Teo, Yong Chua ^a  

^a NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; DIMETHYL SULFOXIDE; HALIDE; MANGANESE; MANGANESE CHLORIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROLINE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CROSS COUPLING REACTION; QUANTUM YIELD; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 77953683110     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.098     Document Type: Article

References (24)

1. For general reviews, see:. Buchwald S.L., and Jiang L. In: Meijere D., and Diederich A. (Eds). Metal-Catalyzed Cross-Coupling Reactions Vol. 2 (2004), Wiley-VCH, Weinheim 699
2. Beletskaya I.P., and Cheprakov A.V. Coord. Chem. Rev. 248 (2004) 2337
3. Beccalli E.M., Broggini G., Martinelli M., and Sottocornola S. Chem. Rev. 107 (2007) 5318
4. Corbert J.P., and Mignani G. Chem. Rev. 106 (2006) 2651
5. Hartwig J.F. Nature 455 (2009) 314
6. For representative papers on copper-mediated Ullmann aliphatic aminations, see:. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400
7. Lu Z., Twieg R.J., and Huang S. Tetrahedron Lett. 44 (2003) 6289
8. Ma D., Cai Q., and Zhang H. Org. Lett. 5 (2003) 2453
9. Okano K., Tokuyama H., and Fukuyama T. Org. Lett. 5 (2003) 4987
10. Jiang D., Fu H., Jiang Y., and Zhao Y. J. Org. Chem. 72 (2007) 672
11. Rout L., Jammi S., and Punniyamurthy T. Org. Lett. 9 (2007) 3397
12. Chen S., Huang H., Liu X., Shen J., Jiang H., and Liu H. J. Comb. Chem. 10 (2008) 358
13. For representative papers on palladium-mediated C-N bond formation, see:. Hartwig J.F. Angew. Chem., Int. Ed. 37 (1998) 2046
14. Barluenga J., Aznar F., and Valdes C. Angew. Chem., Int. Ed. 43 (2004) 343
15. Wagaw S., and Buchwald S.L. J. Org. Chem. 61 (1996) 7240
16. Buchwald S.L., Mauger C., Mignani G., and Scholz U. Adv. Synth. Catal. 348 (2006) 23
17. Anderson K.W., Tundel R.E., Ikawa T., Altman R.A., and Buchwald S.L. Angew. Chem., Int. Ed. 45 (2006) 6523
18. For representative papers on nickel-mediated C-N bond formation, see:. Manolikakes G., Gavryushin A., and Knochel P. J. Org. Chem. 73 (2008) 1429
19. Gao C.-Y., and Yang L.-M. J. Org. Chem. 73 (2008) 1624
20. Correa A., and Bolm C. Angew. Chem., Int. Ed. 46 (2007) 8862
21. Correa A., and Bolm C. Adv. Synth. Catal. 350 (2008) 391
22. Guo D., He H., Xu J., Jiang H., and Liu H. Org. Lett. 10 (2008) 4513
23. Teo Y.-C., Yong F.-F., Poh C.-Y., Yan Y.-K., and Chua G.-L. Chem. Commun. (2009) 6258
24. 2O (99.99% Sigma) under the optimized reaction conditions to afford the product in a good yield of 68%. This excluded the participation of Cu and other metal contaminants that might be present in the Mn salt.