Oxidative amidation of aldehydes and alcohols with primary amines catalyzed by KI-TBHP

European Journal of Organic Chemistry

Volumn , Issue 21, 2008, Pages 3619-3622

  Rajender Reddy, K ^a   Uma Maheswari, C ^a   Venkateshwar, M ^a   Lakshmi Kantam, M ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Alcohols; Aldehydes; Oxidative amidation; Potassium iodide; Primary amines

Indexed keywords

EID: 53749095842     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800454     Document Type: Article

References (41)

1. R. C. Larock in Comprehensive Organic Transformations, WILEY-VCH, New York, 2nd ed., 1999.
2. a) N. Sewald, H.-D. Jakubke in Peptides: Chemistry and Biology, Wiley-VCH, Weinheim, Germany, 2002;
3. b) I. Johansson in Kirk-Othmer Encyclopedia of Chemical Technology: Amides, Fatty Acids (Ed.: J. I. Kroschwitz), 5th ed., Wiley, Hoboken, NJ, 2004, v. 2, pp. 442-463.
4. a) J. M. Humphrey, A. R. Chanberlin, Chem. Rev. 1997, 97, 2243-2266;
5. b) M. Bodanszky in Peptide Chemistry: A Practical Textbook, Springer-Verlag: New York, 1993;
6. c) R.M. Al-Zoubi, O. Marion, D. G. Hall, Angew. Chem. Int. Ed. 2008, 47, 2876-2879;
7. d) B. S. Jursic, Z. Zdravkovski, Synth. Commun. 1993, 23, 2761-2770.
8. a) Y. S. Lin, H. Alper, Angew. Chem. Int. Ed. 2001, 40, 779-781;
9. b) Y. Uozumi, T. Arii, T. Watanabe, J. Org. Chem. 2001, 66, 5272-5274;
10. c) P. Namayakkara, H. Alper, Chem. Commun. 2003, 2384-2385.
11. M. Beller, B. Cornils, C. D. Frohning, J. Mol. Catal. A 1995, 104, 17-18.
12. a) D. Knapton, T. Y. Meyer, Org. Lett. 2004, 6, 687-689;
13. b) Y. Uenoyama, T. Fukuyama, O. Nobuta, H. Matsubara, I. Ryu, Angew. Chem. Int. Ed. 2005, 44, 1075-1078;
14. c) S. Cho, E. Yoo, I. Bae, S. Chang, J. Am. Chem. Soc. 2005, 127, 16046-16047;
15. d) M. P. Cassidy, J. Raushel, V. V. Fokin, Angew. Chem. Int. Ed. 2006, 45, 3154-3157.
16. a) B. L. Nilson, L. L. Kiessling, R. T. Raines, Org. Lett. 2000, 2, 1939-1940;
17. b) N. Shangguan, S. Katukojvala, R. Greenberg, L. J. Williams, J. Am. Chem. Soc. 2003, 125, 7754-7755;
18. c) R. Merkx, A. J. Brouwer, D. T. S. Rijkers, R. M. J. Liskamp, Org. Lett. 2005, 7, 1125-1128.
19. L. Yao, J. Aubé, J. Am. Chem. Soc. 2007, 129, 2766-2767.
20. E. Shaabani, E. Soleimani, A. H. Rezayan, Tetrahedron Lett. 2007, 48, 6137-6141.
21. C. H. Leung, A. M. Voutchkova, R. H. Crabtree, D. Balcells, O. Eisenstein, Green Chem. 2007, 9, 976-979.
22. a) J. W. Bode, S. S. Sohn, J. Am. Chem. Soc. 2007, 129, 13798-13799;
23. b) H. U. Vora, T. Rovis, J. Am. Chem. Soc. 2007, 129, 13796-13797.
24. K. Nakagawa, H. Onoue, K. Minami, Chem. Commun. (London) 1966, 17-18.
25. Y. Tamaru, Y. Yamada, Z. Yoshida, Synthesis 1983, 474-476.
26. a) T. Noata, S. I. Murahashi, Synlett 1991, 693-695;
27. b) A. Tillack, I. Rudloff, M. Beller, Eur. J. Org. Chem. 2001, 523-528.
28. W. J. Yoo, C. J. Li, J. Am. Chem. Soc. 2006, 128, 13064-13065.
29. K. Ekoue-Kovi, C. Wolf, Org. Lett. 2007, 9, 3429-3432.
30. S. Y. Seo, T. J. Marks, Org. Lett. 2008, 10, 317-319.
31. C. Gunanathan, Y. B. David, D. Milstein, Science 2007, 317, 790-792.
32. H. Togo, S. Iida, Synlett 2006, 2159-2175.
33. N. Mori, H. Togo, Tetrahedron 2005, 61, 5915-5925.
34. Preliminary results have been communicated for publication in Synthesis.
35. In the case of oxidative amidation of aromatic aldehydes with benzylamines, it is observed that a fraction of the benzylamine derivatives are converted into their corresponding aldehydes, resulting in a mixture of amide products, which were analyzed by NMR spectroscopy and gas chromatography.
36. B. M. Dean, M. P. V. Mijovi, J. Walker, J. Chem. Soc. 1961, 3394-3400.
37. M. W. Williams, G. T. Young, J. Chem. Soc. 1963, 881-889.
38. K. Nadia, B. Malika, K. Nawel, B. MedYazid, R. Zine, N.-E. Aouf, J. Heterocycl. Chem. 2004, 41, 57-60.
39. K. Y. Lee, Y. H. Kim, M. S. Park, C. Y. Oh, W. H. Ham, J. Org. Chem. 1999, 64, 9450-9458.
40. S. Yamada, D. Morizono, K. Yamamoto, Tetrahedron Lett. 1992, 33, 4329-4332.
41. Oxidative amidation of primary amines with catalytic amounts of iodine (2.5 mol-%) and TBHP for various aldehydes have provided the coupled product in good yield, and the results will be communicated in due course.