Dendrimers and hyperbranched polymers as high-loading supports for organic synthesis

Chemistry - A European Journal

Volumn 7, Issue 2, 2001, Pages 327-335

  Haag, Rainer ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Combinatorial chemistry; Dendrimers; Hybride polymers; Hyperbranched polymers; Solid phase synthesis

Indexed keywords

DENDRIMER; GLYCEROL; GLYCOL; MACROGOL; POLYMER; POLYSTYRENE; REAGENT; RESIN;

CATALYST; COMBINATORIAL CHEMISTRY; REVIEW; SYNTHESIS;

EID: 0035910539     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010119)7:2<327::AID-CHEM327>3.0.CO;2-M     Document Type: Article

References (93)

1. For reviews see: a) D. E. Bergbreiter, Med. Res. Rev. 1999, 19, 439-450;
2. b) S. F. Olivier, C. Abell, Curr. Opin. Chem. Biol. 1999, 3, 299-306;
3. c) S. R. Wilson, A. W. Czarnik, Combinatorial Chemistry, Wiley, New York, 1997;
4. d) J. S. Früchtel, G. Jung, Angew. Chem. 1996, 108, 19-46; Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42;
5. d) J. S. Früchtel, G. Jung, Angew. Chem. 1996, 108, 19-46; Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42;
6. e) F. Balkenhohl, C. von dem Busche-Hünnenfeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; L. A. Tompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-600.
7. e) F. Balkenhohl, C. von dem Busche-Hünnenfeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; L. A. Tompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-600.
8. e) F. Balkenhohl, C. von dem Busche-Hünnenfeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; L. A. Tompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-600.
9. R. B. Merrifield, J. Am. Chem. Soc. 1963, 85, 2149-2154.
10. C. Watson, Angew. Chem. 1999, 111, 2025-2031; Angew. Chem. Int. Ed. 1999, 38, 1903-1908; and references therein.
11. C. Watson, Angew. Chem. 1999, 111, 2025-2031; Angew. Chem. Int. Ed. 1999, 38, 1903-1908; and references therein.
12. P. Hodge, Chem. Soc. Rev. 1997, 26, 417-424; and references therein.
13. A number of copolymers of styrene with various cross-linking agents have been investigated, with precise control of the physicochemical properties. For an overview, see: F. Zaragoza, Organic Synthesis on Solid Phase, Wiley-VCH, Weinheim, 2000.
14. For an example see: S. P. Raillard, G. Ji, A. D. Mann, T. A. Baer, Org. Process Res. Dev. 1999, 3, 177-183.
15. a) For a recent review see: A. Kirschning, H. Monenschein, R. Wittenberg, Angew. Chem. 2000, 112, in press; Angew. Chem. Int. Ed. 2000, 39, in press; and references therein;
16. a) For a recent review see: A. Kirschning, H. Monenschein, R. Wittenberg, Angew. Chem. 2000, 112, in press; Angew. Chem. Int. Ed. 2000, 39, in press; and references therein;
17. b) D. C. Sherrington, Chem. Commun. 1998, 2275-2286.
18. For recent examples of PEGylated resins in organic synthesis see: a) C. Schmitz, M. T. Reetz, Org. Lett. 1999, 1, 1729-1731;
19. b) S. R. McAlpine, S. L. Schreiber, Chem. Eur. J. 1999, 5, 3528-3532;
20. c) A. Boeijen, R. M. J. Liskamp, Eur. J. Org. Chem. 1999, 5, 2127-2135.
21. For example TentaGel is a widely used polystyrene resine with grafted polyethylene glycol chains (Rapp Polymere, Tübingen, Germany), see also ref. [8].
22. a) V. Swali, N. J. Wells, G. J. Langley, M. Bradley, J. Org. Chem. 1997, 62, 4902-4903;
23. b) P. Bharathi, J. S. Moore, J. Am. Chem. Soc. 1997, 119, 3391-3392;
24. c) A. Mahajan, S. R. Chhabra, W. C. Chan, Tetrahedron Lett. 1999, 40, 4909-4912;
25. d) P. Arya, N. V. Rao, J. Singkhonrat, J. Org. Chem. 2000, 65, 1881-1885;
26. e) C. Fromont, M. Bradley, Chem. Commun. 2000, 283-284.
27. A. G. M. Barrett, S. M. Cramp, R. S. Roberts, Org. Lett. 1999, 1, 1083-1086.
28. a) M. Mutter, E. Baeyer, Angew. Chem. 1974, 86, 101-102; Angew. Chem. Int. Ed. Engl. 1974, 13, 88-89;
29. a) M. Mutter, E. Baeyer, Angew. Chem. 1974, 86, 101-102; Angew. Chem. Int. Ed. Engl. 1974, 13, 88-89;
30. b) M. Mutter, R. Uhmann, E. Baeyer, Liebigs Ann. Chem. 1975, 901-915;
31. c) N. K. Mathur, C. K. Narang, R. E. Williams, Polymers as aids in organic chemistry, Academic Press, New York, 1980.
32. For reviews see: a) K. E. Geckeler, Adv. Polym. Sci. 1995, 121, 31-79; and references therein;
33. b) D. J. Gravert, K. D. Janda, Chem. Rev. 1997, 97, 489-509 and references therein;
34. c) P. Wentworth, K. D. Janda, Chem. Commun. 1999, 1917-1924 and references therein.
35. a) H. Frank, H. Hagenmaier, Experientia 1975, 31, 131-133;
36. b) H. Han, K. D. Janda, Angew. Chem. 1997, 109, 1835-1837; Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733 and references therein.
37. b) H. Han, K. D. Janda, Angew. Chem. 1997, 109, 1835-1837; Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733 and references therein.
38. For a review on separation strategies see: D. P. Curran, Angew. Chem. 1998, 110, 1231-1255; Angew. Chem. Int. Ed. 1998, 37, 1174-1196.
39. For a review on separation strategies see: D. P. Curran, Angew. Chem. 1998, 110, 1231-1255; Angew. Chem. Int. Ed. 1998, 37, 1174-1196.
40. For reviews see: a) H. Determann, K. Lampert, Mitt. Dtsch. Pharmaz. Ges. 1970, 40, 117-134;
41. b) D. Paul, Chem. unserer Zeit 1998, 32, 197-205.
42. a) M. Benaglia, R. Annunziata, M. Cinquini, F. Cozzi, S. Ressel, J. Org. Chem. 1998, 63, 8628-8629;
43. b) R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, Chem. Eur. J. 2000, 6, 133-138.
44. R. Knischka, P. Lutz, A. Sunder, R. Mülhaupt, H. Frey, Macromolecules 2000, 33, 315-320.
45. N. N. Reed, K. D. Janda, Org. Lett. 2000, 2, 1311-1313.
46. a) H. Schott, F. Brandstetter, E. Bayer, Makromol. Chem. 1973, 173, 247-251;
47. b) H. Schott, Angew. Chem. 1973, 85, 263-264; Angew. Chem. Int. Ed. Engl. 1973, 12, 246-247;
48. b) H. Schott, Angew. Chem. 1973, 85, 263-264; Angew. Chem. Int. Ed. Engl. 1973, 12, 246-247;
49. b) F. Brandstetter, H. Schott, E. Bayer, Makromol. Chem. 1975, 176, 2163-2175.
50. -1, however, the conversions for the acetal formation even under harsh reaction conditions are typically below 80% and result in complex product mixtures. See also H. G. Elias, An Introduction to Polymer Science, VCH, Weinheim, 1997, p. 163.
51. For examples see: a) D. A. Wellings, A. Williams, Reactive Polymers 1987, 6, 143-157; E. Ranucci, G. Spagnoli, L. Sartore, P. Ferruti, P. Caliceti, O. Schiavon, F. Veronese, Makromol. Chem. Phys. 1994, 195, 3469-3479.
52. For examples see: a) D. A. Wellings, A. Williams, Reactive Polymers 1987, 6, 143-157; E. Ranucci, G. Spagnoli, L. Sartore, P. Ferruti, P. Caliceti, O. Schiavon, F. Veronese, Makromol. Chem. Phys. 1994, 195, 3469-3479.
53. a) G. M. Bonora, A. Baldan, O. Schavon, P. Ferruti, F. M. Veronese, Tetrahedron Lett. 1996, 37, 4761-4764;
54. b) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Palcic, Chem. Commun. 1994, 1849-1850.
55. A. G. M. Barrett, S. M. Cramp, R. S. Roberts, F. J. Zecri, Org. Lett. 1999, 1, 579-582.
56. a) T. Arnauld, A. G. M. Barrett, S. M. Cramp, R. S. Roberts, F. J. Zécri, Org. Lett. 2000, 2, 2663-2666;
57. b) A. G. M. Barrett, S. M. Cramp, R. S. Roberts, F. J. Zécri, Org. Lett. 2000, 2, 261-264;
58. c) A. G. M. Barrett, S. M. Cramp, R. S. Roberts, F. J. Zécri, Comb. Chem. High Throughput Screening 2000, 3, 131-133.
59. For recent reviews see: a) G. R. Newkome, C. N. Moorefield, F. Vögtle, Dendritic Molecules: Concepts, Syntheses, Perspectives, VCH, Weinheim, Germany, 1996;
60. b) M. Fischer, F. Vögtle, Angew. Chem. 1999, 111, 934-955; Angew. Chem. Int. Ed. 1999, 38, 884-905;
61. b) M. Fischer, F. Vögtle, Angew. Chem. 1999, 111, 934-955; Angew. Chem. Int. Ed. 1999, 38, 884-905;
62. c) A. W. Bosman, H. M. Janssen, E. W. Meijer, Chem. Rev. 1999, 99, 1665-1688.
63. Commercially available dendrimers are: polyamine dendrimers (Astramol, DSM) and polyamidoamine dendrimers (Starburst, Dendritec).
64. R. M. Kim, M. Manna, S. M. Hutchins, P. R. Griffin, N. A. Yates, A. M. Bernick, K. T. Chapman, Proc. Natl. Acad. Sci. USA 1996, 93, 10012-10017.
65. A. Sunder, J. Heinemann, H. Frey, Chem. Eur. J. 2000, 6, 2499-2505.
66. Commercially available hyperbranched polymers posses in some cases low molecular weights and are usually less defined with broad molecular weight distributions. Examples are Polyethylenimine (BASF), Boltorn polyesters (Perstorp) and Hybrane polyesteramides (DSM). For a recent review see: R. Haag, H. Frey in Encyclopedia of Materials, Science and Technology, Elsevier, New York, 2001.
67. a) M. Jayaraman, J. M. J. Fréchet, J. Am. Chem. Soc. 1998, 120, 12 996-12 997;
68. b) S. M. Grayson, M. Jayaraman, J. M. Fréchet, Chem. Commun. 1999, 1329-1330.
69. R. Haag, A. Sunder, J.-F. Stumbé, J. Am. Chem. Soc. 2000, 122, 2954-2955.
70. a) C. Bolm, N. Derrien, A. Seger, Chem. Commun. 1999, 2087-2088;
71. b) C. Bolm, N. Derrien, A. Seger, Synlett 1996, 387-388.
72. For recent examples see: a) D. de Groot, E. B. Eggeling, J. C. de Wilde, H. Kooijman, R. J. van Haaren, A. W. van der Made, A. L. Spek, D. Vogt, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, Chem. Commun. 1999, 1623-1624;
73. b) N. J. Hovestad, E. B. Eggeling, H. J. Heidbuchel, J. T. B. H. Jastrzebski, U. Kragl, W. Keim, D. Vogt, G. van Koten, Angew. Chem. 1999, 111, 1763-1765; Angew. Chem. Int. Ed. 1999, 38, 1655-1658;
74. b) N. J. Hovestad, E. B. Eggeling, H. J. Heidbuchel, J. T. B. H. Jastrzebski, U. Kragl, W. Keim, D. Vogt, G. van Koten, Angew. Chem. 1999, 111, 1763-1765; Angew. Chem. Int. Ed. 1999, 38, 1655-1658;
75. c) N. Brinkmann, D. Giebel, G. Lohmer, M. T. Reetz, U. Kragl, J. Catal. 1999, 183, 163-168.
76. A. W. Kleij, R. A. Gossage, J. T. B. H. Jastrzebski, J. Boersma, G. van Koten, Angew. Chem. 2000, 112, 179-181; Angew. Chem. Int. Ed. 2000, 39, 176-178.
77. A. W. Kleij, R. A. Gossage, J. T. B. H. Jastrzebski, J. Boersma, G. van Koten, Angew. Chem. 2000, 112, 179-181; Angew. Chem. Int. Ed. 2000, 39, 176-178.
78. a) A. Sunder, R. Hanselmann, H. Frey, R. Mülhaupt, Macromolecules 1999, 32, 4240-4246;
79. b) A. Sunder, R. Mülhaupt, R. Haag, H. Frey, Macromolecules 2000, 33, 253-254.
80. Currently these polymerizations are carried out on a 500 g scale, further scale-up and commercialization are under investigation.
81. n< 1.8) have been achieved: H. Kautz, A. Sunder, H. Frey, Macromol. Symp. 2000, in press.
82. R. Haag, J. F. Stumbé, A. Sunder, H. Frey, A. Hebel, Macromolecules 2000, 33, 8158-8166.
83. A. Sunder, H. Türk, R. Haag, H. Frey, Macromolecules 2000, 7682-7692.
84. A. Sunder, R. Mülhaupt, R. Haag, H. Frey, Adv. Mater. 2000, 12, 235-239.
85. A. B. Kantchev, J. R. Parquette, Tetrahedron Lett. 1999, 40, 8049-8053.
86. R. Haag, A. Sunder, A. Hebel, S. Roller, 2000, unpublished results.
87. A. Burgath, A. Sunder, H. Frey, Macromol. Chem. Phys. 2000, 201, 782-791.
88. -1): a) C. C. Leznoff, J. Y. Wong, Can. J. Chem. 1973, 51, 3756-3764;
89. b) C. C. Leznoff, S. Greenberg, Can. J. Chem. 1976, 54, 3824-3829;
90. c) P. Hodge, J. Waterhouse, J. Chem. Soc. Perkin Trans. I 1983, 2319-2323; on glass supports:
91. d) U. Maskos, E. M. Southern, Nucl. Acids Res. 1992, 20, 1679-1684; with photocleavable linkers:
92. e) M. J. Aurell, C. Vboix, M. L. Ceita, C. Llopis, A. Tortajada, R. Mestres, J. Chem. Res. 1995, 2569-2583; for the coupling of steoroidal ketones:
93. f) R. Maltais, M. Bérubé, O. Marion, R. Labrecque, D. Poirier, Tetrahedron Lett. 2000, 41, 1691-1694.