Combinatorial Methods for the Discovery and Optimisation of Homogeneous Catalysts

Abstract

The use of combinatorial methods to discover new catalysts is one of the youngest fields of combinatorial chemistry. The main focus of this review is the application of combinatorial liquid- and solid-phase methods for the discovery and optimisation of homogeneous catalysts. In addition, high-throughput screening techniques for fast detection of activity and selectivity in catalytic reactions are discussed. The literature from 1995 to December 2000 is covered.

• 1 Introduction

• 2 Methods in Combinatorial Catalysis

• 3 Combinatorial Liquid-Phase Methods

• 3.1 Reaction Examples

• 3.1.1 Carbene Insertion

• 3.1.2 Reductive Aldol Reaction

• 3.1.3 Michael Addition

• 3.1.4 Diethyl Zinc Addition to Aldehydes

• 3.1.5 Aza-Diels-Alder Reaction

• 3.2 Modular Ligand Systems for Homogeneous Metal Catalysis

• 4 Combinatorial Solid-Phase Methods

• 4.1 Screening for Metal Binders

• 4.2 Catalysts in C-C Bond Formation

• 4.2.1 Diethyl Zinc Addition to Aldehydes

• 4.2.2 Addition of Trimethylsilylcyanide to meso-Epoxides

• 4.2.3 Asymmetric Strecker Reaction

• 4.2.4 Allylic Substitution Reactions

• 4.3 Catalytic Oxidation and Reduction Reactions

• 4.3.1 Alkene Epoxidation

• 4.3.2 Catalytic Hydrogenation

• 4.4 Catalytic Phosphate Hydrolysis

• 5 High-Throughput Screening in Catalysis

• 5.1 IR-Thermography

• 5.2 Isotope Labelling/Pseudo Enantiomers

• 5.3 Fluorescence Assays

• 5.4 Reactive Dyes

• 5.5 One-pot Multi Substrate Screening

• 5.6 Screening of Mixtures of Catalysts

• 5.7 Miscellaneous Chromatographic Methods

• 6 Conclusion

combinatorial catalysis - catalysis - combinatorial chemistry - asymmetric catalysis - high-throughput screening

References

1 Balkenhohl F. von dem Bussche-Hünnefeld C. Lansky A. Zechel C. Angew. Chem., Int. Ed. Engl.  1996,  35:  2289 

2 Früchtel JS. Jung G. Angew. Chem. Int. Ed. Engl.  1996,  35:  17 

3 Combinatorial Chemistry   Jung G. Wiley-VCH; Weinheim: 1999. 

4 Furka Á. Sebestyén F. Asgedom M. Dibó G. In 14th International Congress of Biochemistry (Prague)   VSP, Utrecht; The Netherlands: 1988.  p.47 

5

Combs, A. P. In Second Annual Boston College ArQule Symposium on Combinatorial Chemistry Boston, 2000.

6 Briceño G. Change H. Sun X. Schultz PG. Xiang X.-D. Science  1995,  273 

7 For a review of combinatorial methods in material science: Jandeleit B. Schäfer DJ. Powers TS. Turner HW. Weinberg WH. Angew. Chem. Int. Ed.  1999,  38:  2494 

8 Gennari C. Nestler HP. Piarulli U. Salom B. Liebigs Ann./Recueil  1997,  637 

9 Brocchini S. James K. Tangpasuthadol JV. Kohn J. J. Am. Chem. Soc.  1997,  119:  4553 

10 Shuttleworth SJ. Allin SM. Wilson RD. Nasturica D. Synthesis  2000,  1035 

11 During the preparation of this manuscript, a review concentrating on ”Combinatorial and Evolution-Based Methods in the Creation of Enantioselective Catalysts" was published: Reetz MT. Angew. Chem. Int. Ed.  2001,  40:  312 

12 Snapper ML. Hoveyda AH. In Combinatorial Chemistry   Fenniri H. Oxford University Press; Oxford: 2000.  p.433 

13 Kagan HB. J. Organomet. Chem.  1998,  567:  3 

14 Crabtree RH. Chem. Commun.  1999,  1611 

15 Bein T. Curr. Opin. Sol. State Mat. Sci.  1999,  4:  85 

16 Bein T. Angew. Chem. Int. Ed.  1999,  38:  323 

17 Maier WF. Kirsten G. Orschel M. Weiss PA. Chim. Oggi  2000,  18:  15 

18 Gennari F. Seneci P. Miertus S. Catal. Rev. Sci. Engl.  2000,  42:  385 

19 Shimizu KD. Snapper ML. Hoveyda AH. Chem.-Eur. J.  1998,  4:  1885 

20 Burgess K. Lim HS. Porte AM. Sulikowski GA . Angew. Chem. Int. Ed. Engl.  1996,  35:  220 

21

(CuOTf)C₆H₆ and sparteine in THF were used.

22

[Rh(nbd)]BPh₄ and sparteine in toluene were used.

23 Taylor SJ. Morken JP. J. Am. Chem. Soc.  1999,  121:  12202 

24

Abbrevations: i-Pr-pybox = 2,6-bis(4-isopropyl-2-oxazolin-2-yl)pyridine, t-Bu-box = 2,2"-isopropylidenebis(4-tert-butyl-2-oxazoline), Ph-semicorrin = 4-phenyl-α-[4-phenyloxazolidin-2-ylidene]-2-oxazoline-2-acetonitrile, MOP = 2-(diphenylphosphino-2"-methoxy)-1,1"-binaphthyl, BINAP = 2,2"-bis(diphenylphosphino)-1,1"-binaphthyl, DuPhos = 1,2-bis(2,5-dimethylphospholano)benzene, quinap = 1-(2-diphenylphosphino-1-naphtyl)isoquinoline, cod = cyclooctadiene.

25 Christoffers J. Mann A. Angew. Chem. Int. Ed.  2000,  39:  2752 

26 Soai K. Niwa S. Chem. Rev.  1992,  92:  833 

27 Kitamura M. Hirosama SS. Noyori R. J. Am. Chem. Soc.  1998,  120:  9800 

28 Ding K. Ishii A. Mikami K. Angew. Chem. Int. Ed.  1999,  38:  497 

29 Hattori K. Yamamoto H. Synlett  1993,  129 

30 Hattori K. Yamamoto H. Tetrahedron  1993,  49:  1749 

31 Jørgensen KA. Angew. Chem. Int. Ed.  2000,  39:  3558 

32 Bromidge S. Wilson PC. Whiting A. Tetrahedron Lett.  1998,  39:  8905 

33 Hayashi T. In Ferrocenes   Togni A. Hayashi T. VCH; Weinheim: 1995.  p.105 

34 Togni A. Angew. Chem. Int. Ed. Engl.  1996,  35:  1475 

35 Richards CJ. Locke AJ. Tetrahedron: Asymmetry  1998,  9:  2377 

36 von Matt P. Pfaltz A. Angew. Chem. Int. Ed. Engl.  1993,  32:  655 

37 Sprinz J. Helmchen G. Tetrahedron Lett.  1993,  34:  1769 

38 Dawson GJ. Frost CG. Williams JMJ. Coote SJ. Tetrahedron Lett.  1993,  34:  3149 

39 Takada H. Ohe K. Uemura S. Angew. Chem. Int. Ed.  1999,  38:  1288 

40 Helmchen G. Pfaltz A. Acc. Chem. Res.  2000,  33:  336 

41 Noyori R. Takaya H. Acc. Chem. Res.  1990,  23:  345 

42 Nozaki K. Sakai N. Nanno T. Higashijma T. Mano S. Horiushi T. Takaya H. J. Am. Chem. Soc.  1997,  119:  4413 

43 Uozumi Y. Tanahashi A. Lee S.-Y. Hayashi T. J. Org. Chem.  1993,  58:  1945 

44 Lipshutz BH. Shin Y.-J. Tetrahedron Lett.  1998,  39:  7017 

45 Selvakumar K. Valentini M. Wörle M. Pregosin PS. Albinati A. Organometallics  1999,  18:  1207 

46 Jacobsen EN. Zhang W. Muci AR. Ecker JR. Deng L. J. Am. Chem. Soc.  1991,  113:  7063 

47 Zhang W. Loebach JL. Wilson SR. Jacobsen EN. J. Am. Chem. Soc.  1990,  112:  2801 

48 Palucki M. McCormick GJ. Jacobsen EN. Tetrahedron Lett.  1995,  36:  5457 

49 Brandes BD. Jacobsen EN. Tetrahedron Lett.  1995,  36:  5123 

50 Li Z. Conser KR. Jacobsen EN. J. Am. Chem. Soc.  1993,  115:  5326 

51 O"Connor KJ. Wey S.-J. Burrows CJ. Tetrahedron Lett.  1992,  33:  1001 

52 Fukuda T. Katsuki T. Synlett  1995,  825 

53 Lam F. Xu JX. Chan KS. J. Org. Chem.  1996,  61:  8414 

54 Pfenninger A. Synthesis  1986,  89 

55 Sharpless KB. Behrens CH. Katsuki T. Lee AWM. Martin VS. Taktani M. Viti SM. Walker FJ. Woodard SS. Pure Appl. Chem.  1983,  55:  589 

56 Pfaltz A. Acta Chem. Scand.  1996,  50:  189 

57 Porte AM. Reibenspies J. Burgess K. J. Am. Chem. Soc.  1998,  120:  9180 

58 Kranich R. Eis K. Geis O. Mühle S. Bats JW. Schmalz H.-G. Chem.-Eur. J.  2000,  6:  2874 

59 Francis MB. Finney NS. Jacobsen EN. J. Am. Chem. Soc.  1996,  118:  8983 

60 Lin G. Ellman JA. J. Org. Chem.  1995,  60:  7712 

61 Gennari C. Ceccarelli S. Piarulli U. Montalbetti CAGN. Jackson RFW. J. Org. Chem.  1998,  63:  5312 

62 Brouwer AJ. van der Linden HJ. Liskamp RMJ. J. Org. Chem.  2000,  65:  1750 

63 Gao X. Kagan HB. Chirality  1998,  10:  120 

64 Cole BM. Shimizu KD. Krueger CA. Harrity JPA. Snapper ML. Hoveyda AH. Angew. Chem. Int. Ed. Engl.  1996,  35:  1668 

65 Shimizu KD. Cole BM. Krueger CA. Kuntz KW. Snapper ML. Hoveyda AH. Angew. Chem. Int. Ed. Engl.  1997,  36:  1704 

66 Sigman MS. Jacobsen EN. J. Am. Chem. Soc.  1998,  120:  4901 

67 Sigman MS. Vachal P. Jacobsen EN. Angew. Chem. Int. Ed.  2000,  39:  1279 

68 Gilbertson SR. Collibee SE. Agrakov A. J. Am. Chem. Soc.  2000,  122:  6522 

69 Francis MB. Jacobsen EN. Angew. Chem. Int. Ed.  1999,  38:  937 

70 Gilbertson SR. Wang X. Tetrahedron  1999,  55:  11609 

71

The relationship between the two phosphine-containing amino acids is determined by their relative position in the peptide sequence. If the first is placed in the position i of the peptide sequence, the second is e.g. in the i+4 position. In this case three other amino acids are positioned between them.

72 Menger FM. Eliseev AV. Migulin VA. J. Org. Chem.  1995,  60:  6666 

73 Scanlan TS. Prudent JR. Schultz PG. J. Am. Chem. Soc.  1991,  113:  9397 

74 Menger FM. Ding J. Barragan V. J. Org. Chem.  1998,  63:  7578 

75 Berkessel A. Hérault DA. Angew. Chem. Int. Ed.  1999,  38:  102 

76 Berkessel A. Riedel R. J. Comb. Chem.  2000,  2:  215 

77 Taylor SJ. Morken JP. Science  1998,  280:  267 

78 Reetz MT. Becker MH. Kühling KM. Holzwarth A. Angew. Chem. Int. Ed.  1998,  37:  2647 

79 Reetz MT. Becker MH. Liebl M. Fürstner A. Angew. Chem. Int. Ed.  2000,  39:  1236 

80 Grubbs RH. Chang S. Tetrahedron  1998,  54:  4413 

81 Fürstner A. Top. Catal.  1998,  4:  285 

82 Fürstner A. Top. Organomet. Chem.  1998,  1:  37 

83 Schuster M. Blechert S. Angew. Chem. Int. Ed. Engl.  1997,  36:  2036 

84 Reetz MT. Becker MH. Klein H.-W. Stöckigt D. Angew. Chem. Int. Ed.  1999,  38:  1758 

85 Horeau A. Nouaille A. Tetrahedron Lett.  1990,  31:  2707 

86 Guo J. Wu J. Siuzdak G. Finn MG. Angew. Chem. Int. Ed.  1999,  38:  1755 

87 Shaughnessy KH. Kim P. Hartwig JF. J. Am. Chem. Soc.  1999,  121:  2123 

88 Copeland KH. Miller SJ. J. Am. Chem. Soc.  1999,  121:  4306 

89 Cooper AC. McAlexander LH. Lee D.-H. Torres MT. Crabtree RH. J. Am. Chem. Soc.  1998,  120:  9971 

90 Herrmann WA. Brossmer C. Reisinger C.-P. Riermeier TH. Öfele K. Beller M. Chem.-Eur. J.  1997,  3:  1357 

91 Corey EJ. Bakshi RK. Shibati S. J. Am. Chem. Soc.  1987,  109:  5551 

92 Mikami K. Angelaud R. Ding K. Ishii A. Tanaka A. Sawada N. Kudo K. Senda M. Chem.-Eur. J.  2001,  7:  730 

93 Reetz MT. Kühling KM. Deege A. Hinrichs H. Belder D. Angew. Chem. Int. Ed.  2000,  39:  3891 

94

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