Design and assembly of virtual homogeneous catalyst libraries - Towards in silico catalyst optimisation

Advanced Synthesis and Catalysis

Volumn 348, Issue 3, 2006, Pages 361-369

  Hageman, Jos A ^a   Westerhuis, Johan A ^a   Frühauf, Hans Werner ^b   Rothenberg, Gadi ^b  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Catalyst discovery; Hydroformylation; Ligand design; Molecular descriptors; QSAR; Virtual library

Indexed keywords

EID: 33644594632     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505299     Document Type: Article

References (49)

1. For a recent and excellent general monograph on homogeneous catalysis see P. W. N. M. van Leeuwen, Homogeneous Catalysis: Understanding the Art, Kluwer, Dordrecht, 2004.
2. M. Thommen, H.-U. Blaser, Chim. Oggi 2003, 21, 6.
3. For a recent collection of essays on the principles and practice of THE, see: a) High-Throughput Synthesis, (Ed.: I. Sucholeiki), Marcel Dekker, New York, 2001;
4. for reviews on applying HTE in homogeneous catalysis, see: b) M. T. Reetz, Angew. Chem. Int. Ed. 2001, 40, 284, and references cited therein;
5. for applications in heterogeneous catalysis, see: c) S. Senkan, Angew. Chem. Int. Ed. 2001, 40, 312;
6. d) A. Holzwarth, P. Denton, H. Zanthoff, C. Mirodatos, Catalysis Today 2001, 67, 309.
7. For a modular approach to constructing chiral ligands, see: F. Spindler, C. Malan, M. Lotz, M. Kesselgruber, U. Pittelkow, A. Rivas-Nass, O. Briel, H.-U. Blaser, Tetrahedron: Asymmetry 2004, 15, 2299.
8. There are many reports on applications of HTE methods in catalysis, but relatively few commercial successes. An exception is the Pd-phosphinous acid systems discovered by Li and colleagues from DuPont's Combiphos, see: G. Y. Li, Chemical Industries (CRC Press), 2005, 104, (Catal. Org. React.) 177.
9. G. Y. Li, J. Org. Chem. 2002, 67, 3643.
10. L. Chen, M. W. Deem, J. Chem. Inform. Comp. Sci. 2001, 41, 950.
11. This premise applies just as well to heterogeneous catalysis, where the situation is further complicated by the plethora of parameters that must be taken into account in HTE catalyst preparation and treatment steps. See, for example a) C. Klanner, D. Farrusseng, L. Baumes, M. Lengliz, C. Mirodatos, F. Schüth, Angew. Chem. Int. Ed. 2004, 43, 5347;
12. b) C. Klanner, D. Farrusseng, L. Baumes, C. Mirodatos, F. Schüth, QSAR Comb. Sci. 2003, 22, 729.
13. For a discussion on combining selection algorithms and THE, see: J. A. Westerhuis, H. F. M. Boelens, D. Iron, G. Rothenberg, Anal. Chem. 2004, 76, 3171.
14. H. Bönnemann, Angew. Chem. Int. Ed. Engl. 1985, 24, 248.
15. K. D. Cooney, T. R. Cundari, N. W. Hoffman, K. A. Pittard, M. D. Temple, Y. Zhao, J. Am. Chem. Soc. 2003, 125, 4318.
16. E. Burello, G. Rothenberg, Adv. Synth. Catal. 2003, 345, 1334.
17. E. Burello, D. Farrusseng, G. Rothenberg, Adv. Synth. Catal. 2004, 346, 1844.
18. E. Burello, P. Marion, J. C. Galland, A. Chamard, G. Rothenberg, Adv. Synth. Catal. 2005, 347, 803.
19. For an excellent review on measuring chemical similarity/diversity, see: N. Nikolova, J. Jaworska, QSAR Comb. Sci. 2003, 22, 1006.
20. For an application of such global search methods, see: J. A. Hageman, R. Wehrens, H. A. Van Sprang, L. M. C. Buydens, Anal. Chim. Acta 2003, 490, 211.
21. For a discussion on choosing molecular descriptors for virtual screening, see: L. Xue, J. Bajorath, Comb. Chem. High Throughput Scr. 2000, 3.
22. P. W. N. M. van Leeuwen, P. C. J. Kamer, J. N. H. Reek, Pure Appl. Chem. 1999, 71, 1443.
23. P. Dierkes, P. W. N. M. Van Leeuwen, J. Chem. Soc. Dalton Trans. 1999, 1519.
24. For a review on the properties of non-phosphine chelate ligands, see: K. J. Cavell, Aust. J. Chem. 1994, 47, 769.
25. For a discussion on the natural bite angle of diphosphines, see: C. P. Casey, G. T. Whiteker, Isr. J. Chem. 1990, 30, 299.
26. For a comparison between 2D and 3D descriptors in homogeneous catalysis, see: E. Burello, G. Rothenberg, Adv. Synth. Catal. 2005, 347, 1969-1977.
27. Even using state-of-the-art hydroformylation catalysts, optimisation of process conditions is still a challenge; see: P. B. Webb, T. E. Kunene, D. J. Cole-Hamilton, Green Chem. 2005, 7, 373.
28. D. F. Foster, D. Gudmunsen, D. J. Adams, A. M. Stuart, E. G. Hope, D. J. Cole-Hamilton, G. P. Schwarz, P. Pogorzelec, Tetrahedron 2002, 58, 3901.
29. P. Cheliatsidou, D. F. S. White, D. J. Cole-Hamilton, Dalton Trans. 2004, 3425.
30. Z. Freixa, P. W. N. M. Van Leeuwen, Dalton Trans. 2003, 1890.
31. Z. Freixa, M. S. Beentjes, G. D. Batema, C. B. Dieleman, G. P. F. van Strijdonck, J. N. H. Reek, P. C. J. Kamer, J. Fraanje, K. Goubitz, P. W. N. M. van Leeuwen, Angew. Chem. Int. Ed. 2003, 42, 1284.
32. M. Matsumoto, M. Tamura, J. Mol. Catal. 1982, 16, 209.
33. M. T. Reetz, S. R. Waldvogel, R. Goddard, Tetrahedron Lett. 1997, 38, 5967.
34. J. I. van der Vlugt, R. Sablong, P. C. M. M. Magusin, A. M. Mills, A. L. Spek, D. Vogt, Organometallics 2004, 23, 3177.
35. R. P. J. Bronger, J. P. Bermon, J. Herwig, P. C. J. Kamer, P. W. N. M. Van Leeuwen, Adv. Synth. Catal. 2004, 346, 789.
36. C. P. Casey, G. T. Whiteker, M. G. Melville, L. M. Petrovich, J. A. Gavney, Jr., D. R. Powell, J. Am. Chem. Soc. 1992, 114, 5535.
37. For a general discussion on regression variable selection, see: A. J. Burnham, J. F. MacGregor, R. Viveros, J. Chemom. 2001, 15, 265.
38. J. Niu, G. Yu, Environ. Toxicol. Pharmacol. 2004, 18, 39.
39. M. Randic, J. Am. Chem. Soc. 1975, 97, 6609.
40. H. Wiener, J. Am. Chem. Soc. 1947, 69, 17.
41. L. B. Kier, L. H. Hall, Eur. J. Med. Chem. 1977, #20#12, 307.
42. N. S. Zefirov, M. A. Kirpichenok, F. F. Izmailov, M. I. Trofimov, Dokl. Akad. Nauk SSSR 1987, 296, 883.
43. M. A. Kirpichenok, N. S. Zefirov, Zh. Org. Khim. 1987, 23.
44. J. A. Hageman, R. Wehrens, R. de Gelder, W. Leo Meerts, L. M. C. Buydens, J. Mol. Phys. 2000, 113, 7955.
45. J. A. Hageman, M. Streppel, R. Wehrens, L. M. C. Buydens, J. Chemom. 2003, 17, 427.
46. MATLAB™ is commercially available from MathWorks, Natick USA, version 6.1, 2001.
47. HyperChem™ Professional 7.51, Hypercube, Inc., 1115 NW 4th Street, Gainesville, Florida 32601, USA.
48. For a detailed description of regression methods, see: a) B. G. M. Vandeginste, D. L. Massart, L. M. C. Buydens, S. d. Jong, P. J. Lewi, J. Smeyers-Verbeke, Handbook of chemometrics, Vol. 20B, Elsevier, Amsterdam, 1998;
49. for a specific tutorial on PLS regression, see: b) P. Geladi, B. R. Kowalski, Anal. Chim. Acta 1986, 185, 1.