Aqueous N-alkylation of amines using alkyl halides: Direct generation of tertiary amines under microwave irradiation

Green Chemistry

Volumn 6, Issue 4, 2004, Pages 219-221

  Ju, Yuhong ^a   Varma, Rajender S ^a  

^a U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; HALIDE;

ALKYLATION; AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL BOND; HEATING; MICROWAVE IRRADIATION; PHASE TRANSITION; SYNTHESIS;

EID: 2342635028     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b401620c     Document Type: Article

References (24)

1. (a) A. Seayad, M. Ahmed, H. Klein, R. Jackstell, T. Gross and M. Beller, Science, 2002, 297, 1676;
2. (b) F. Y. Rachinskii, T. G. Potapenko, O. D. Shapilov, V. T. Osipyan and A. A. Krupenina, USSR, Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1968, 41, 1072;
3. (c) F. Kiuchi, S. Nishizawa, H. Kawanishi, S. Kinoshita, H. Ohsima, A. Uchitani, N. Sekino, M. Ishida, K. Kondo and Y. Tsuda, Chem. Pharm. Bull. Jpn., 1992, 40, 3234.
4. T. E. Muller and M. Beller, Chem. Rev., 1998, 98, 675.
5. W. J. Hickinbottom, J. Chem. Soc., 1930, 992.
6. S. Caspe, J. Am. Chem. Soc., 1932, 54, 4457.
7. F. Ullmann, Ber. Dtsch. Chem. Ges., 1903, 36, 2382.
8. I. Goldberg, Ber. Dtsch. Chem. Ges., 1906, 39, 1691.
9. (a) B. Y. Yang and S. L. Buchwald, J. Organomet. Chem., 1999, 576, 125;
10. (b) J. F. Hartwig, Angew. Chem., Int. Ed., 1998, 37, 2406.
11. L. Shi, M. Wang, C.-A. Fan, F.-M. Zhang and Y.-Q. Tu, Org. Lett., 2003, 5, 3515.
12. C. Gabriel, S. Gabriel, E. H. Grant, B. S. J. Halstead and D. M. P. Mingos, Chem. Soc. Rev., 1998, 27, 213.
13. M. Larhed, C. Moberg and A. Hallberg, Acc. Chem. Res., 2002, 35, 717.
14. (a) R. S. Varma, Organic Synthesis using Microwaves and Supported Reagents in Microwaves in Organic Synthesis, ed. A. Loupy, Wiley-VCH, Weinheim, 2002, pp. 181;
15. (b) R. S. Varma, Advances in Green Chemistry: Chemical Syntheses Using Microwave Irradiation, AstraZeneca Research Foundation India, Bangalore, India, 2002 (free copy available from: azrefi@astrazeneca.com).
16. (c) R. S. Varma, Pure Appl. Chem., 2001, 73, 193;
17. (d) R. S. Varma, Green Chem., 1999, 1, 43.
18. (a) D. Bogdal, J. Pielichowski and K. Jaskot, Heterocycles, 1997, 45, 715;
19. (b) P. de la Cruz, A. de la Hoz, L. M. Font, F. Langa and M. C. Perez-Rodriguez, Tetrahedron Lett., 1998, 39, 6053.
20. J. March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, John Wiley & Sons, Inc., New York, 1992, pp. 370.
21. V. V. Namboodiri and R. S. Varma, Green Chem., 2001, 3, 146.
22. B. L. Hayes, Microwave Synthesis - Chemistry at the Speed of Light, CEM Publishing, Mathews, NC, 2002, pp. 29-36.
23. (a) C. J. Li and T. H. Chan, Organic Reaction in Aqueous Media, John Wiley & Sons, New York, 1997;
24. (b) C. J. Li, Chem. Rev., 1993, 93, 2023.