Mechanism of the organocatalyzed decarboxylative Knoevenagel-Doebner reaction. A theoretical study

Journal of Physical Chemistry A

Volumn 114, Issue 50, 2010, Pages 13086-13092

  Bermúdez, Eduardo ^a   Ventura, Oscar N ^a   Méndez, Patricia Saenz ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CARBOXYLATION;

BASIS SETS; BULK SOLVENTS; GASPHASE; KNOEVENAGEL CONDENSATION; NUCLEOPHILIC ATTACK; SECONDARY AMINES; THEORETICAL STUDY; TRANSITION STATE;

DENSITY FUNCTIONAL THEORY;

EID: 84961979098     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp109703f     Document Type: Article

References (47)

1. Gentile, A.; Giordano, C.; Fuganti, C.; Ghirotto, L.; Servi, S. J. Org. Chem. 1992, 57, 6635-6637
2. Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Sadao, T. Tetrahedron: Asymmetry 2000, 11, 4485-4497
3. Hatfield, R.; Vermerris, W. Plant Physiol. 2001, 126, 1351-1357
4. Graf, E. Free Radical Biol. Med. 1992, 13, 435-448
5. Kikuzaki, H.; Hisamoto, M.; Hirose, K.; Akiyama, K.; Taniguchi, H. J. Agric. Food Chem. 2002, 50, 2161-2168
6. Nenandis, N.; Zhang, H.-Y.; Tsimidou, M. Z. J. Agric. Food Chem. 2003, 51, 1874-1879
7. McNulty, J.; Steere, J. A.; Wolf, S. Tetrahedron Lett. 1998, 39, 8013-8016
8. Mitra, A. K.; De, A.; Karchaudhuri, N. Synth. Commun. 1999, 29, 573-581
9. Kaupp, G.; Naimi-Jamal, M. R.; Schmeyers, J. Tetrahedron 2003, 59, 3753-3760
10. List, B.; Doehring, A.; Hechavarria Fonseca, M. T.; Job, A.; Rios Torres, R. Tetrahedron 2006, 62, 476-482
11. Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243-4244
12. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726-3748
13. Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501
14. MacMillan, D. W. C. Nature 2008, 455, 304-308
15. Tilay, A.; Bule, M.; Kishenkumar, J.; Annapure, U. J. Agric. Food Chem. 2008, 56, 7644-7648
16. Pan, G. X.; Bolton, J. L.; Leary, G. J. J. Agric. Food Chem. 1998, 46, 5283-5288
17. Ralph, J.; Lundquist, K.; Brunow, G.; Lu, F.; H., K.; Schatz, P. F.; Marita, J. M.; Hatfield, R.; Ralph, S. A.; Christensen, J. H.; Boerjan, W. Phytochem. Rev. 2004, 3, 29-60
18. Ragauskas, A. J.; Williams, C. K.; Davison, B. H.; Britovsek, G.; Cairney, J.; Eckert, C. A.; Frederick, W. J.; Hallet, J. P.; Leak, D. J.; Liotta, C. L.; Mielenz, J. R.; Murphy, R.; Templer, R.; Tschaplinski, T. Science 2006, 311, 484-489
19. Simpson, C. J.; Fitzhenry, M. J.; Stamford, N. P. J. Tetrahedron Lett. 2005, 46, 6893-6896
20. M.Ames, J.; Macleod, G. Phytochemistry 1990, 29, 1201-1207
21. Chung, H. Y. J. Agric. Food Chem. 2000, 48, 1803-1809
22. Pihlsgård, P.; Larsson, M.; Leufvén, A.; Lingnert, H. J. Agric. Food Chem. 2000, 48, 4844-4850
23. Janes, D.; Kantar, D.; Kreft, S.; Prosen, H. Food Chem. 2009, 112, 120-124
24. Cong, R.; Pelton, R.; Russo, P.; Doucet, G. Macromolecules 2002, 36, 204-209
25. Aslam, S. N.; Stevenson, P. C.; Phythian, S. J.; Veitch, N. C.; Hall, D. R. Tetrahedron 2006, 62, 4214-4226
26. Sinha, A. K.; Sharma, A.; Joshi, B. P. Tetrahedron 2007, 63, 960-965
27. Wang, Y.; Shang, Z.-c.; Wu, T.-x.; Fan, J.-c.; Chen, X. J. Mol. Catal. A: Chem. 2006, 253, 212-221
28. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford Science Publications: Oxford, 1989.
29. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377
30. Hehre, W. J.; Radom, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
31. Foresman, J. B.; Frisch, Æ. Exploring Chemistry with Electronic Structure Methods; Gaussian, Inc.: Pittsburgh, PA, 1996.
32. Jensen, F. Introduction to Computational Chemistry; Wiley: Chichester, West Sussex, England, 1999.
33. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161
34. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527
35. Miertus, S.; Scrocco, E.; Tomasi J. Chem. Phys. 1981, 55, 117-129
36. Miertus, S.; Tomasi J. Chem. Phys. 1982, 65, 239-245
37. Tomasi, J.; Perisco, M. Chem. Rev. 1994, 94, 2027-2094
38. Barone, V.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404-417
39. Frisch, M.; J; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, B.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
40. Tietze, L. F.; Beifuss, U. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2; pp 341 - 394.
41. List, B. Tetrahedron 2002, 58, 5573-5590
42. Lynch, B. J.; Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2003, 107, 1384-1388
43. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423-2425
44. Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209
45. Coghe, S.; Benoot, K.; Delvaux, F.; Vanderhaegen, B.; Delvaux, F. R. J. Agric. Food Chem. 2004, 52, 602-608
46. Vanbeneden, N.; Gils, F.; Delvaux, F.; Delvaux, F. R. Food Chem. 2008, 107, 221-230
47. Szabados, L.; Savouré, A. Trends Plant Sci. 2010, 15, 89-97