Iodine catalyzed Mukaiyama-Michael reaction: Experimental evaluation of catalytic effect in conjunction with computational study of the reaction mechanism

Journal of Physical Organic Chemistry

Volumn 25, Issue 12, 2012, Pages 1228-1235

  Deuri, Sanjib ^a   Phukan, Prodeep ^a  

^a GAUHATI UNIVERSITY   (India)

Author keywords

density functional theory; electrophilicity; molecular iodine; Mukaiyama Michael addition; nucleophilicity

Indexed keywords

BOND FORMATION PROCESS; CATALYTIC EFFECTS; CATALYZED REACTIONS; COMPUTATIONAL STUDIES; CONCEPTUAL DENSITY FUNCTIONAL THEORY; ELECTROPHILICITY; ENOLATES; EXPERIMENTAL EVALUATION; LOW ACTIVATION; METHYL VINYL KETONES; MODEL SYSTEM; MOLECULAR IODINE; MUKAIYAMA-MICHAEL ADDITION; NUCLEOPHILICITIES; REACTION MECHANISM; REACTIVITY DESCRIPTORS; TRIHYDROSILYL ENOL ETHER; UNCATALYZED REACTIONS; UNSATURATED KETONES;

ADDITION REACTIONS; ALDEHYDES; CATALYSIS; CHEMICAL BONDS; ETHERS; ETHYLENE; IODINE; KETONES; ORGANIC COMPOUNDS;

DENSITY FUNCTIONAL THEORY;

EID: 84872079131     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.2997     Document Type: Article

References (62)

1. K. Narasaka, K. Soai, T. Mukaiyama, Chem. Lett. 1974, 1223.
2. K. Narasaka, K. Soai, Y. Aikawa, T. Mukaiyama, Bull. Chem. Soc. Jpn. 1976, 49, 779.
3. K. Saigo, M. Osaki, T. Mukaiyam, Chem. Lett. 1976, 163.
4. T. Sato, Y. Wakahara, J. Otera, H. Nozaki, J. Am. Chem. Soc. 1991, 113, 4028.
5. P. Duhamel, G. Dujardin, L. Hennequin, J. M. Poirier, J. Chem. Soc. Perkin Trans. 1 1992, 387.
6. B. D. Gray, J. D. White, J. Chem. Soc. Chem. Commun. 1985, 20.
7. H. Hagiwara, A. Okano, T. Akama, H. Uda, J. Chem. Soc. Chem. Commun. 1987, 1333.
8. P. Weghe, J. Collin, Tetrahedron Lett. 1993, 34, 3881.
9. A. Kawada, S. Mitamma, S. Kobayashi, Chem. Commun. 1996, 183.
10. C. L. Roux, G. Itoughmane, J. Dubac, J. Jaud, P. Vignaux, J. Org. Chem. 1993, 58, 1835.
11. P. A. Grieco, W. J. Dubay, L. J. Todd, J. Org. Chem. 1994, 59, 6898.
12. S. Fukuzumi, T. Okamoto, K. Yasui, T. Suenobu, S. Itoh, J. Otera, Chem. Lett. 1997, 667.
13. P. A. Grieco, J. J. Nunes, M. A. Gaul, W. P. Dailey, J. Am. Chem. Soc. 1991, 113, 2761.
14. T. Mukaiyama, M. Tamora, S. Kobayashi, Chem. Lett. 1986, 1817.
15. T. Yura, N. Iwasawa, K. Narasaka, T. Mukaiyama, Chem. Lett. 1988, 1025.
16. T. Sato, Y. Wakahara, J. Otera, H. Nojaki, Tetrahedron 1991, 47, 9773.
17. S. Kobayashi, I. Hachiya, H. Ishitani, M. Araki, Synlett. 1993, 472.
18. K. Ishihara, N. Hananki, H. Yamamoto, Synlett. 1993, 577.
19. Y. Kita, J. Segawa, J. Hamita, T. Fujii, Y. Tamura, Tetrahedron Lett. 1980, 21, 3779.
20. K. Mastumoto, Angew. Chem. Int. Ed. Eng. 1980, 19, 1013.
21. Y. Kita, J. Segawa, J. Hasuta, H. Yasuda, Y. Tamura, J. Chem. Soc. Perkin Trans. 1 1982, 1099.
22. T. V. Rajan Babu, J. Org. Chem. 1984, 49, 2083.
23. Y. Genisson, L. Gorrichon, Tetrahedron Lett. 1994, 35, 233.
24. C. T. Wong, M. W. Wong, J. Org. Chem. 2005, 70, 124.
25. C. T. Wong, M. W. Wong, J. Org. Chem. 2007, 72, 1425.
26. L. Wang, M. W. Wong, Tetrahedron Lett. 2008, 49, 3916.
27. T. K. Hollis, B. Bosnich, J. Am. Chem. Soc. 1995, 117, 4570.
28. S. E. Denmark, C. T. Chen, Tetrahedron Lett. 1994, 35, 4327.
29. S. E. Denmark, W. Lee, J. Org. Chem. 1994, 59, 707.
30. T. Sato, Y. Wakahara, J. Otera, H. Nozaki, S. Fukuzumi, J. Am. Chem. Soc. 1991, 113, 4028.
31. J. Otera, Y. Fujita, T. Sato, H. Nozaki, S. Fukuzumi, M. Fujita, J. Org. Chem. 1992, 57, 5054.
32. S. Fukuzumi, M. Fujita, J. Otera, Y. Fujita, J. Am. Chem. Soc. 1992, 114, 10271.
33. J. Otera, Y. Fujita, N. Sakuta, M. Fujita, S. Fukuzumi, J. Org. Chem. 1996, 61, 2951.
34. S. Das, R. Borah, R. R. Devi, A. J. Thakur, Synlett. 2008, 2741.
35. H. Togo, S. Iida, Synlett. 2006, 2159.
36. M. Jereb, D. Vražič, M. Zupan, Tetrahedron 2011, 67, 1355.
37. P. Phukan, J. Org. Chem. 2004, 69, 4005.
38. P. Phukan, Tetrahedron Lett. 2004, 45, 4785.
39. P. Phukan, Synth. Commun. 2004, 34, 1065.
40. P. Phukan, D. Kataki, P. Chakraborty, Tetrahedron Lett. 2006, 47, 5523.
41. D. Kataki, P. Phukan, Ind. J. Chem. 2006, 45B, 1759.
42. D. Kataki, P. Chakraborty, P. Sarmah, P. Phukan, Ind. J. Chem. Technol. 2006, 13, 519.
43. D. Kataki, P. Phukan, Tetrahderon Lett. 2009, 50, 1958.
44. R. G. Parr, W. Yang,. Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
45. P. Geerlings, F. De Proft, W. Langenaeker, Chem. Rev. 2003, 103, 1793.
46. P. K. Chattaraj, U. Sarkar, D. R. Roy, Chem. Rev. 2006, 106, 2065.
47. R. G. Parr, R. G. Pearson, J. Am. Chem. Soc. 1983, 105, 7512.
48. R. G. Parr, L. Von Szentpaly, S. Liu, J. Am. Chem. Soc. 1999, 121, 1922.
49. L. R. Domingo, E. Chamorro, P. Perez, J. Org. Chem. 2008, 73, 4615.
50. P. Jaramillo, L. R. Domingo, E. Chamorro, P. Perez, J. Mol. Struct. (THEOCHEM) 2008, 865, 68.
51. S. Deuri, P. Phukan,. J. Mol. Struct. (THEOCHEM) 2010, 945, 64.
52. S. Deuri, P. Phukan,. Ind. J. Chem. 2010, 49A, 1206.
53. Becke, A. D. J., Chem. Phys. 1993, 98, 5648.
54. M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. Elbert, M. S. Gordon, J. J. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupis, J. A. Montegomery, J. Comput. Chem. 1993, 14, 1347.
55. B. M. Bode, M. S. Gordon, J. Mol. Graphics. Mod. 1999, 16,133.
56. C. González, H. B. Schelegel, J. Chem. Phys. 1991, 95, 5853.
57. M. W. Wong, Chem. Phys. Lett. 1996, 256, 391.
58. A. R. Vaino, W. A. Szavk, Chem. Commun. 1996, 2351.
59. B. Alcaide, P. Almendros, G. Cabrero, R. Callejo, M. P. Ruiz, M. Arnõ, L. R. Domingo, Adv. Synth. Catal. 2010, 352, 1688.
60. J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry, Oxford University Press, New York, 2001.
61. Y. Xia, C. Rong, Q. Xu, D. Yin, S. Liu, J. Phys. Chem. A 2008, 112, 9970.
62. X. Y. Li, J. Nie, J. Phys. Chem. A 2008, 112, 9970.