The power of high-throughput experimentation in homogeneous catalysis research for fine chemicals

European Journal of Organic Chemistry

Volumn , Issue 5, 2003, Pages 799-811

  De Vries, Johannes G ^a   De Vries, André H M ^a  

^a DSM RESEARCH   (Netherlands)

Author keywords

Aromatic substitution; Asymmetric catalysis; High throughput screening; Homogeneous catalysis; Palladium

Indexed keywords

LIGAND; PHOSPHORAMIDIC ACID;

CATALYSIS; CATALYST; CHEMICAL REACTION; HECK REACTION; HYDROGENATION; MEDICAL RESEARCH; SHORT SURVEY; STOICHIOMETRY;

EID: 0037335777     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Short Survey

References (98)

1. Applied Homogeneous Catalysis with Organometallic Compounds, vol. 1 and 2 (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996.
2. J. G. de Vries, in Encyclopedia of Catalysis (Ed.: I. Horvath), Wiley, New York, 2002, web-edition.
3. Transition Metals for Organic Synthesis; Building Blocks and Fine Chemicals, vol. 1 and 2 (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998.
4. R. A. Sheldon, J. Mol. Catal. A: Chem. 1996, 107, 75-83.
5. This percentage is based on the personal observations of the authors.
6. See also: H.-U. Blaser, B. Pugin, F. Spindler, in Applied Homogeneous Catalysis with Organometallic Compounds, vol. 2 (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996, pp. 992-1009.
7. C. Mercier, P. Chabardes, Pure Appl. Chem. 1994, 66, 1509-1518.
8. H. Kumobayashi, Recl. Trav. Chim. Pays-Bas 1996, 115, 201-210.
9. [9a] H.-U. Blaser, H.-P. Buser, K. Coers, R. Hanreich, H. P. Jalett, E. Jelsch, B. Pugin, H.-D. Schneider, F. Spiondler, A. Wegmann, Chimia 1999, 53, 275-280.
10. [9b] H.-U. Blaser, Adv. Synth. Catal. 2002, 344, 17-31.
11. C. E. Tucker, J. G. de Vries, Top. Catal. 2002, 19, 111-118.
12. [11a] M. van den Berg, A. J. Minnaard, E. P. Schudde, J. van Esch, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, J. Am. Chem. Soc. 2000, 122, 11539-11540.
13. [11b] M. van den Berg, A. J. Minnaard, B. L. Feringa, J. G. de Vries, Catalyst for asymmetric (transfer) hydrogenation, WO 02 04466, January 17, 2002.
14. [11c] M. van den Berg, R. M. Haak, A. J. Minnaard, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Adv. Synth. Catal. 2002, 344, 1003-1007.
15. [11d] M. van den Berg, A. J. Minnaard, R. M. Haak, M. Leeman, E. P. Schudde, A. Meetsma, B. L. Feringa, A. H. M. de Vries, C. E. P. Maljaars, C. E. Willans, D. Hyett, J. A. F. Boogers, H. J. W. Henderickx, J. G. de Vries, Adv. Synth. Catal. 2003, 345, 308-323.
16. Combinatorial Chemistry. Synthesis, Analysis, Screening (Ed.: G. Jung), Wiley-VCH, Weinheim, 1999.
17. K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889.
18. R. H. Crabtree, Chem. Commun. 1999, 1611-1616.
19. A. Hagemeyer, B. Jandeleit, Y. Liu, D. M. Poojary, H. W. Turner, A. F. Volpe, Jr., W. H. Weinberg, Appl. Catal A: General 2001, 221, 23-43.
20. M. Reetz, Angew. Chem. Int. Ed. 2001, 40, 284-310.
21. S. Dahmen, S. Bräse, Synthesis 2001, 1431-1449.
22. A. Hoveyda, in Handbook of Combinatorial Chemistry, vol. 2 (Eds.: K. C. Nicolaou, R. Hanko, W. Hartwig), Wiley-VCH, Weinheim, 2002, pp. 991-1016.
23. There are exceptions. See: C. Hinderling, P. Chen, Angew. Chem. Int. Ed. 1999, 38, 2253-2256; Angew. Chem. 1999, 111, 2393-2396.
24. There are exceptions. See: C. Hinderling, P. Chen, Angew. Chem. Int. Ed. 1999, 38, 2253-2256; Angew. Chem. 1999, 111, 2393-2396.
25. J. M. Newsam, F. Schüth, Biotechnol. Bioeng. 1998/1999, 61, 203-216.
26. B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. Int. Ed. 1999, 38, 2494-2532; Angew. Chem. 1999, 111, 2648-2689.
27. B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. Int. Ed. 1999, 38, 2494-2532; Angew. Chem. 1999, 111, 2648-2689.
28. M. Larhed, C. Moberg, A. Hallberg, Acc. Chem. Res. 2002, 35, 717-727.
29. M. Eckert, U. Notheis, in Handbook of Combinatorial Chemistry, vol. 2 (Eds.: K. C. Nicolaou, R. Hanko, W. Hartwig), Wiley-VCH, Weinheim, 2002, pp. 831-863.
30. O. Brümmer, B. Jandeleit, T. Uno, W. H. Weinberg, in Handbook of Combinatorial Chemistry, vol. 2 (Eds.: K. C. Nicolaou, R. Hanko, W. Hartwig), Wiley-VCH, Weinheim, 2002, pp. 864-884.
31. B. Archibald, O. Brümmer, M. Devenney, S. Gorer, B. Jandeleit, T. Uno, W. H. Weinberg, T. Weskamp, in Handbook of Combinatorial Chemistry, vol. 2 (Eds.: K. C. Nicolaou, R. Hanko, W. Hartwig), Wiley-VCH, Weinheim, 2002, pp. 885-990.
32. M. Bauser, H. Stakemeier, in Handbook of Combinatorial Chemistry, vol. 1 (Eds.: K. C. Nicolaou, R. Hanko, W. Hartwig), Wiley-VCH, Weinheim, 2002, pp. 190-224.
33. [27a] A. C. Cooper, L. H. McAlexander, D.-H. Lee, M. T. Torres, R. H. Crabtree, J. Am. Chem. Soc. 1998, 120, 9971-9972.
34. [28b] G. T. Copeland, S. J. Miller, J. Am. Chem. Soc. 1999, 121, 4306-4307.
35. [28c] K. H. Shaughnessy, P. Kim, J. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123-2132.
36. [28d] O. Lavastre, J. P. Morken, Angew. Chem. Int. Ed. 1999, 38, 3163-3165; Angew. Chem. 1999, 111, 3357-3359.
37. [28d] O. Lavastre, J. P. Morken, Angew. Chem. Int. Ed. 1999, 38, 3163-3165; Angew. Chem. 1999, 111, 3357-3359.
38. [28a] A. Holzwarth, H.-W. Schmidt, W. F. Maier, Angew. Chem. Int. Ed. 1998, 37, 2644-2647; Angew. Chem. 1998, 110, 2788-2792.
39. [28b] A. Holzwarth, H.-W. Schmidt, W. F. Maier, Angew. Chem. Int. Ed. 1998, 37, 2644-2647; Angew. Chem. 1998, 110, 2788-2792.
40. [28b] M. T. Reetz, M. H. Becker, K. M. Kühling, A. Holzwarth, Angew. Chem. Int. Ed. 1998, 37, 2647-2650; Angew. Chem. 1998, 110, 2792-2795.
41. [28b] M. T. Reetz, M. H. Becker, K. M. Kühling, A. Holzwarth, Angew. Chem. Int. Ed. 1998, 37, 2647-2650; Angew. Chem. 1998, 110, 2792-2795.
42. D. B. Kassel, Chem. Rev. 2001, 101, 255-267.
43. S. Senkan, K. Krantz, S. Ozturk, V. Zerngin, I. Onal, Angew. Chem. Int. Ed. 1999, 38, 2794-2799; Angew. Chem. 1999, 111, 2965-2971.
44. S. Senkan, K. Krantz, S. Ozturk, V. Zerngin, I. Onal, Angew. Chem. Int. Ed. 1999, 38, 2794-2799; Angew. Chem. 1999, 111, 2965-2971.
45. For a highlight summarising recent developments, see: M. T. Reetz, Angew. Chem. Int. Ed. 2002, 41, 1335-1338.
46. K. Burgess, H.-J. Lim, A. M. Porte, G. A. Sulikowski, Angew. Chem. Int. Ed. Engl. 1996, 35, 220-222; Angew. Chem. 1996, 108, 192-194.
47. K. Burgess, H.-J. Lim, A. M. Porte, G. A. Sulikowski, Angew. Chem. Int. Ed. Engl. 1996, 35, 220-222; Angew. Chem. 1996, 108, 192-194.
48. M. B. Francis, E. N. Jacobsen, Angew. Chem. Int. Ed. 1999, 38, 937-941; Angew. Chem. 1999, 111, 987-991.
49. M. B. Francis, E. N. Jacobsen, Angew. Chem. Int. Ed. 1999, 38, 937-941; Angew. Chem. 1999, 111, 987-991.
50. S. J. Taylor, J. P. Morken, J. Am. Chem. Soc. 1999, 121, 12202-12203.
51. M. S. Stephan, A. J. J. M. Teunissen, G. K. M. Verzijl, J. G. de Vries, Angew. Chem. Int. Ed. 1998, 37, 662-664; Angew. Chem. 1998, 110, 688-690.
52. M. S. Stephan, A. J. J. M. Teunissen, G. K. M. Verzijl, J. G. de Vries, Angew. Chem. Int. Ed. 1998, 37, 662-664; Angew. Chem. 1998, 110, 688-690.
53. F. Kakiuchi and S. Murai, in Topics in Organometallic Chemistry, vol. 3 (Ed.: S. Murai), Springer-Verlag, Berlin, 1999, pp. 47-79.
54. C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639.
55. M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586-1587.
56. F. Diederich, P. J. Stang, Metal-catalysed Cross-coupling Reactions, Wiley-VCH, Weinheim, 1998.
57. J. G. de Vries, Can. J Chem. 2001, 79, 1086-1092.
58. I. P. Beletskaya, A. V Cheprakov, Chem. Rev. 2000, 100, 3009-3066.
59. [42a] F. J. Parlevliet, A. H. M. de Vries, J. G. de Vries, WO 02/ 00340.
60. [42b] A. H. M. de Vries, F. J. Parlevliet, L. Schmiedervan de Vondervoort, J. H. M. Mommers, H. J. W. Henderickx, M. A. M. Walet, J. G. de Vries, Adv. Synth. Catal. 2002, 344, 996-1002.
61. We assume that the resting state of the catalyst is an anionic PdX-3 species (X = Br, I). See ref. [42b] for details.
62. A kinetic explanation is also possible: Formation of clusters will be higher order in palladium, whereas the Heck reaction will be first- or half-order in palladium, depending on if the resting state is monomeric or dimeric. For a Heck reaction half-order in palladium, see: G. P. F. van Strijdonck, M. D. K. Boele, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, Eur. J. Inorg. Chem. 1999, 1073-1076.
63. A. H. M. de Vries, J. G. de Vries, WO 02/057199, 2002, to DSM nv.
64. H. Geissler, in Transition Metals for Organic Synthesis, vol. 1 (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998, pp. 158-183.
65. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1469. See also a special issue of J. Organomet. Chem. 2002, 653, no. 1-2.
66. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1469. See also a special issue of J. Organomet. Chem. 2002, 653, no. 1-2.
67. [48a] A. Suzuki, in Metal-catalysed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97.
68. [48b] N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
69. [48c] A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90.
70. Phosphanes: A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020-4028, and references therein. Imidazolium salts: G. A. Grasa, M. S. Viciu, J. Huang, C. Zhang, M. L. Trudell, S. P. Nolan, Organometallics 2002, 21, 2866-2873, and references therein.
71. Phosphanes: A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020-4028, and references therein. Imidazolium salts: G. A. Grasa, M. S. Viciu, J. Huang, C. Zhang, M. L. Trudell, S. P. Nolan, Organometallics 2002, 21, 2866-2873, and references therein.
72. [50a] S. Haber, H. J. Kleiner, DE 19527118.
73. [50b] M. Beller, J. G. E. Krauter, A. Zapf, Angew. Chem. Int. Ed. Engl. 1997, 36, 772-774.
74. For ligand-free Suzuki couplings in water or aqueous mixtures (at least 50% water), see: I. P. Beletskaya, Pure Appl. Chem. 1997, 69, 471-476, and references therein.
75. T. I. Wallow, B. M. Novak, J. Org. Chem. 1994, 59, 5034-5037.
76. D. Badone, M. Baroni, R. Cardamone, A. Ielmini, U. Guzzi, J. Org. Chem. 1997, 62, 7170-7173.
77. An earlier example of the use of HTE in the optimisation of a Suzuki raction: E. G. IJpeij, F. H. Beijer, H. J. Arts, C. Newton, J. G. de Vries, G. J. Gruter, J. Org. Chem. 2002, 67, 169-176.
78. 3P-based polymer-supported catalysts in Suzuki couplings, see: T. J. Colacot, E. S. Gore, A. Kuber, Organometallics 2002, 21, 3301-3304.
79. This assumption is valid only when no catalyst deactivation occurs.
80. S. R. Gilbertson, X. Wang, Tetrahedron Lett. 1996, 37, 6475-6478.
81. M. T. Reetz, G. Mehler, Angew. Chem. Int. Ed. 2000, 39, 3889.
82. C. Claver, E. Fernandez, A. Gillon, K. Heslop, D. J. Hyett, A. Martorell, A. G. Orpen, P. G. Pringle, Chem. Commun. 2000, 961.
83. R. Kramer, K. Eis, O. Geis, S. Mühle, J. W. Bats, H.-G. Schmalz, Chem. Eur J. 2000, 6, 2874-2894 and references cited therein.
84. O. Liu, J. A. Ellmann, J. Org. Chem. 1995, 60, 7712-7713.
85. [62a] B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671; Angew. Chem. 1996, 108, 1776-1779.
86. [62a] B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671; Angew. Chem. 1996, 108, 1776-1779.
87. [62b] K. D. Shimizu, B. M. Cole, C. A. Krueger, K. W Kuntz, M. L. Snapper, A. H. Hoeveyda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1704-1707; Angew. Chem. 1997, 109, 1781-1785.
88. [62b] K. D. Shimizu, B. M. Cole, C. A. Krueger, K. W Kuntz, M. L. Snapper, A. H. Hoeveyda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1704-1707; Angew. Chem. 1997, 109, 1781-1785.
89. [63a] M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902.
90. [63b] M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 5315-5316.
91. [64a] C. Gennari, S. Ceccarelli, U. Piarulli, C. A. G. N. Montalbetti, R. F. W. Jackson, J. Org. Chem. 1998, 63, 5312-5313.
92. [64b] I. Chataigner, C. Gennari, U. Piarulli, S. Ceccarelli, Angew. Chem. Int. Ed. 2000, 39, 916-918.
93. A. J. Brouwer, H. J. van der Linden, R. M. J. Liskamp, J. Org. Chem. 2000, 65, 1750-1775.
94. R. A. Johnson, K. B. Sharpless, in Catalytic Asymmetric Synthesis (Ed.: I. Ojina), 2nd ed., Wiley-VCH, New York, 2000, p. 357-398.
95. K. Kacprzak, J. Gawronsky, Synthesis 2001, 961-998.
96. M. Lambers, F. H. Beijer, J. M. Padron, I. Toth, J. G. de Vries, J. Org. Chem. 2002, 67, 5022-5024.
97. European Union-funded RTN network, The Discovery of New Molecular Catalysts through Combinatorial Chemistry. Activity and Selectivity from Diversity, HPRN-CT-2000-00014. See: http://www.oc.uni-koeln.de/berkessel/CombiCat/index.shtml
98. European Union-funded RTN network, Enantioselective Recognition. Towards the Separation of Racemates, HPRN-CT-2001-00182 See: http://www.soton.ac.uk/-jdk1/ecn/