Utilisation of ionic liquid solvents for the synthesis of Lily-of-the-Valley fragrance {β-Lilial®; 3-(4-t-butylphenyl)-2- methylpropanal}

Journal of Molecular Catalysis A: Chemical

Volumn 231, Issue 1-2, 2005, Pages 61-66

  Forsyth, Stewart A ^a   Gunaratne, H Q Nimal ^a   Hardacre, Christopher ^a   McKeown, Angela ^a   Rooney, David W ^a   Seddon, Kenneth R ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

Fragrance; Heck; Ionic liquids; Lilial; Palladium catalyst; Recycling

Indexed keywords

CATALYSIS; CATALYSTS; PALLADIUM; SYNTHESIS (CHEMICAL);

IONIC LIQUID HECK REACTION; IONIC LIQUIDS; N-METHYLPYRROLIDINONE;

ORGANIC SOLVENTS;

2 PYRROLIDONE DERIVATIVE; 3 (4 TERT BUTYLPHENYL) 2 METHYLPROPANAL; BIS(2,3 DIHYDRO 3 METHYLBENZOTHIAZOL 2 YLIDENE)DIIODOPALLADIUM; FRAGRANCE; N METHYLPYRROLIDINONE; ORGANIC SOLVENT; PALLADIUM; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ACRYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CONVALLARIA; HECK REACTION; NANOPARTICLE; SYNTHESIS;

EID: 14844333561     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2004.12.022     Document Type: Article

References (38)

1. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009
2. G.T. Crisp Chem. Soc. Rev. 27 1998 427
3. A. Biffis, M. Zecca, and M. Basato J. Mol. Catal. A 173 2001 249
4. R.F. Heck Palladium Reagents in Organic Synthesis 1985 Academic Press London
5. A. de Meijere, and F.E. Meyer Angew. Chem. 106 1994 2473
6. J. Tsuji Palladium Reagents and Catalysts 1995 Wiley Chichester
7. S. Brase, and A. de Meijere F. Diederich P.J. Stang Metal-Catalyzed Cross-Coupling Reactions 1998 Wiley-VCH Weinheim 99
8. V. Calò, A. Nacci, A. Monopoli, and M. Spinelli Eur. J. Org. Chem. 2003 1382
9. V. Calò, A. Nacci, and A. Monopoli J. Mol. Catal. A 214 2004 45
10. M. Aslam, V. Elango, and K.G. Davenport Synthesis 1989 869
11. J.Y. Goujon, F. Zammattio, and B. Kirschleger Tetrahedron: Asymmetry 11 2000 2409
12. Y. Fumio, H. Toshifumi, W. Masayuki, S. Mitsuro, and S. Masanori Heterocycles 24 1986 1223
13. F. Berthiol, H. Doucet, and M. Santelli Tetrahedron Lett. 45 2004 5633
14. J.B. Melpolder, and R.F. Heck J. Org. Chem. 41 1976 265
15. A.J. Chalk, and S.A. Magennis J. Org. Chem. 41 1976 273
16. S. Bouquillon, B. Ganchegui, B. Estrine, F. Hénin, and J. Muzart J. Organomet. Chem. 364 2001 153
17. E. Bernocchi, S. Cacchi, P.G. Ciattini, E. Morera, and G. Ortar Tetrahedron Lett. 33 1992 3073
18. S. Sengupta, and S.K. Sadhuikhan Tetrahedron Lett. 39 1998 2291
19. A.J. Carmichael, M.J. Earle, J.D. Holbrey, P.B. McCormac, and K.R. Seddon Org. Lett. 1 1999 997
20. W.A. Herrmann, and V.P.W. Böhm J. Organomet. Chem. 572 1999 141
21. L. Xu, W. Chen, and J. Xiao Organometallics 19 2000 1123
22. R.R. Deshmukh, R. Rajagopal, and K.V. Srinivasan Chem. Commun. 2001 1544
23. B.M. Bhanage, and M. Arai Catal. Rev., Sci. Eng. 2001 315
24. L. Djakovitch, M. Wagner, C.G. Hartung, M. Beller, and K. Koehler J. Mol. Catal. A 219 2004 121
25. X.G. Xie, J.P. Lu, B. Chen, J.J. Han, X.G. She, and X.F. Pan Tetrahedron Lett. 45 2004 809
26. H. Hagiwara, Y. Shimizu, T. Hoshi, T. Suzuki, M. Ando, K. Ohkubo, and C. Yokoyama Tetrahedron Lett. 42 2001 4349
27. K. Okubo, M. Shirai, and C. Yokoyama Tetrahedron Lett. 43 2002 7115
28. F. Zhao, B.M. Bhanage, M. Shirai, and M. Arai Chem. Eur. J. 6 2000 843
29. F. Zhao, M. Shirai, and M. Arai J. Mol. Catal. A 154 2000 39
30. J. Jayasaree, A. Seayad, and R.V. Chaudhari Chem. Commun. 1999 1067
31. K. Kohler, R.G. Heidenreich, J.G.E. Krauter, and M. Pietsch Chem. Eur. J. 8 2002 622
32. J.R.W.M. Easter, M.S. Carpenter, US Patent 2,875,131 (1956).
33. D.R. MacFarlane, P. Meakin, J. Sun, N. Amini, and M. Forsyth J. Phys. Chem. B 103 1999 4164
34. V. Calò, R. Del Sole, A. Nacci, E. Schingaro, and F. Scordari Eur. J. Org. Chem. 2000 869
35. N.A. Hamill, C. Hardacre, and S.E.J. McMath Green Chem. 2002 139
36. M.T. Reetz, and M. Maase Adv. Mater. 11 1999 773
37. K. Anderson, Ph.D. Thesis, The Queen's University of Belfast (2004).
38. V. Cimpeanu, V. Parvulescu, P. Amorós, D. Beltrán, J.M. Thompson, and C. Hardacre Eur. Chem. J. 10 2004 4640