Gem-diamines as highly active organocatalysts for carbon-carbon bond formation

Journal of Catalysis

Volumn 246, Issue 1, 2007, Pages 136-146

  Climent, María J ^a   Corma, Avelino ^a   Domínguez, Irene ^a   Iborra, Sara ^a   Sabater, María J ^a   Sastre, Germán ^a  

^a INSTITUTO DE TECNOLOGÍA QUÍMICA   (Spain)

Author keywords

Basic catalysis; Computational chemistry; Gem diamines; Knoevanagel condensation

Indexed keywords

ACTIVATION ENERGY; ALDEHYDES; CARBON; CATALYSTS; CHEMICAL BONDS; CONDENSATION; ORGANOMETALLICS;

BASIC CATALYSIS; BENZALDEHYDE; BOND FORMATION; COMPUTATIONAL CHEMISTRY; KNOEVANAGEL CONDENSATION; PROTON AFFINITY; TRANSITION STATES;

AMINES;

EID: 33846217703     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2006.11.029     Document Type: Article

References (51)

1. Climent M.J., Corma A., Iborra S., and Velty A. J. Catal. 221 (2004) 472
2. Cauvel A., Renard G., and Brunel D. J. Org. Chem. 62 (1997) 749
3. Laspéras M., Llorett T., Chaves L., Rodriguez I., Cauvel A., and Brunel D. Stud. Surf. Sci. Catal. 108 (1997) 75
4. Bigi F., Carloni S., Maggi R., Mazzacani A., and Sartori G. Stud. Surf. Sci. Catal. 130 (2000) 3501
5. Rodriguez I., Iborra S., and Corma A. Appl. Catal. 194-195 (2000) 241
6. Subba Rao Y.V., De Vos D.E., and Jacobs P.A. Angew. Chem. Int. Ed. Engl. 36 (1997) 2661
7. Sercheli R., Vargas R.M., Sheldon R., and Schuchardt U. J. Mol. Catal. A 148 (1999) 173
8. Jaenicke S., Chuah G.K., Lin X.H., and Hu X.C. Microporous Mesoporous Mater. 35-36 (2000) 143
9. Blanc A.C., Macquarrie D.J., Valle S., Renard G., Quinn C.R., and Brunel D. Green Chem. 2 (2000) 383
10. Corma A., Iborra S., Rodriguez I., and Sanchez F. J. Catal. 211 (2002) 208
11. Besse J.-P., Brunel D., Massiani P., and Tichit D. Actual. Chimique 5-6 (2002) 111
12. Alder R.W. Chem. Rev. 89 (1989) 1215
13. Staab H.A., and Saupe T. Angew. Chem Int. Ed. Engl. 27 (1988) 865
14. Llamas-Saiz A.L., Foces-Foces C., and Elguero J. J. Mol. Struct. 328 (1994) 297
15. Rodriguez I., Sastre G., Corma A., and Iborra S. J. Catal. 183 (1999) 14
16. B. Siebenhaar, WO 9721659 (1997)
17. A.J. Kesel, W. Oberthür, WO 9820013 (1998)
18. J.P. Ferraris, T.L. Lambert, S. Rodriguez, WO 9305077 (1993)
19. Corma A., Fornes V., Martin-Aranda R.M., and Rey F. J. Catal. 134 (1992) 58
20. Climent M.J., Corma A., Fornés V., Frau A., Guil-Lopez R., Iborra S., and Primo J. J. Catal. 163 (1996) 392
21. Prout F.S., Beaucaire U.D., Dyrkarcz G.R., Koppes W.M., Kuznicki R.E., Marlewski T.A., Pienkowski J.A., and Puda J.M. J. Org. Chem. 38 (1973) 1512
22. Jones G. Org. React. 15 (1967) 204
23. Guyot J., and Kergomard A. Tetrahedron 39 (1983) 1166
24. V.K. Valerij, G.I. Rutman, USSR SU1482910 (1989)
25. Binkley J.S., Pople J.A., and Hehre W.J. J. Am. Chem. Soc. 102 (1980) 939
26. Gordon M.S., Binkley J.S., Pople J.A., Pietro W.J., and Hehre W.J. J. Am. Chem. Soc. 104 (1982) 2797
27. Pietro W.J., Francl M.M., Hehre W.J., Defrees D.J., Pople J.A., and Binkley J.S. J. Am. Chem. Soc. 104 (1982) 5039
28. Schlegel H.B. J. Comput. Chem. 3 (1982) 214
29. Simons J., Jorgensen P., Taylor H., and Ozment J. J. Phys. Chem. 87 (1983) 2745
30. Bannerjee A., Adams N., Simons J., and Shepard R. J. Phys. Chem. 89 (1985) 52
31. Golab J.T., Yeager D.L., and Jorgensen P. Chem. Phys. 78 (1983) 175
32. Cerjan C.J., and Miller W.H. J. Chem. Phys. 75 (1981) 2800
33. Becke A.D. J. Chem. Phys. 10 (1993) 5648
34. Ditchfield R., Hehre W.J., and Pople J.A. J. Chem. Phys. 54 (1971) 724
35. Hehre W.J., Ditchfield R., and Pople J.A. J. Chem. Phys. 56 (1972) 2257
36. Hariharan P.C., and Pople J.A. Mol. Phys. 27 (1974) 209
37. Gordon M.S. Chem. Phys. Lett. 76 (1980) 163
38. Hariharan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213
39. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Buran, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J.J. Dannenberg, K.D. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A.11.2, Gaussian, Inc., Pittsburgh, PA, 1998
40. Ballini R., Fiorini D., Maggi R., Righi P., Sartori G., and Sartorio R. Green Chem. 5 (2003) 396
41. Van Aken E., Wynberg H., and Van Bolhuis F. Acta Chem. Scand. 47 (1993) 122
42. Bensa D., and Rodriguez J. Synth. Commun. 34 (2004) 1515
43. Horvath A. Tetrahedron Lett. 37 (1996) 4423
44. Jerome F., Kharchafi G., Adam I., and Barrault J. Green Chem. 6 (2004) 7
45. Guimaraes A.L.M., and Vargas R.M. J. Am. Oil Chem. Soc. 75 (1998) 755
46. Schuchardt U., Vargas R.M., and Gelbard G. J. Mol. Catal. A 99 (1995) 65
47. Alder R.W. J. Am. Chem. Soc. 127 21 (2005) 7924
48. Alder R.W., Goode N.C., Miller N., Hibbert F., Hunte K.P.P., and Robbins H.J. J. Chem. Soc. Chem. Commun. (1978) 89
49. Hibbert F., and Simpson G.R. J. Chem. Soc. Perkin Trans. 2 (1987) 243
50. Patai S., and Israeli Y. J. Chem. Soc. (1960) 2025
51. In: Reeves R.L., and Patai S. (Eds). The Chemistry of Carbonyl Group (1966), Interscience, New York 567