Pd catalysis on dendronized solid support: Generation effects and the influence of the backbone structure

Journal of the American Chemical Society

Volumn 129, Issue 18, 2007, Pages 5860-5869

  Dahan, Adi ^a   Portnoy, Moshe ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CROSSLINKING; POLYETHERS; POLYSTYRENES; RESINS;

BACKBONE STRUCTURES; BROMOBENZENE; DENDRONIZED SOLID SUPPORT; SUZUKI REACTION;

PALLADIUM;

BROMOBENZENE; LIGAND; PALLADIUM; PHOSPHINE; POLYMER; POLYSTYRENE; RESIN;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; HECK REACTION; SUZUKI REACTION;

EID: 34248571754     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065265d     Document Type: Article

References (63)

1. See special issue of Chemical Reviews: Recoverable catalysts and reagents. Gladysz, J. A., Guest Ed. Chem. Rev. 2002, 102.
2. (a) McNamara, A. C.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
3. (b) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217.
4. Zaragoza-Dörwald, F. Organic Synthesis on Solid Phase - Supports, Linkers, Reactions, 2nd ed.; Wiley-VCH: Weinheim, 2002.
5. Ley, S. V.; Baxendale, I. R.; Bream. R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 2002, 1, 3815.
6. (a) Dahan, A.; Portnoy, M. Chem. Commun. 2002, 2700.
7. (b) Dahan, A.; Portnoy, M. Org. Lett. 2003, 5, 1197.
8. (c) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc 2000, 122, 956.
9. (d) Alper, H.; Arya, P.; Bourque, S. C.; Jefferson, G. R.; Manzer, L. E. J. Am. Chem. Soc. 2001, 123, 2889.
10. (e) Lu, S.-M.; Alper, H. J. Am. Chem. Soc. 2003, 125, 13126.
11. (f) Bu, J.; Judeh, Z. M. A.; Ching, C. B.; Kawi, S. Catal. Lett. 2003, 85, 183.
12. (g) Chung, Y.-M.; Rhee, H.-K. Chem. Commun. 2002, 238.
13. (a) Frechet, J. M. J.; Tomalia, D. A. Dendrimers and other dendritic-polymers; Wiley-VCH: New York, 2002.
14. (b) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and dendrons: concepts, synthesis, application; Wiley-VCH: Weinheim, 2001.
15. Dahan, A.; Portnoy, M. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 235.
16. (a) Tam, J. P. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5409.
17. (b) Swali, V.; Wells, N. J.; Langley, G. J.; Bradley, M. J. Org. Chem. 1997, 62, 4902.
18. (c) Fromont, C.; Bradley, M. Chem. Commun. 2000, 283.
19. (a) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035.
20. (b) Alper, H.; Arya, P.; Bourque, S. C.; Jefferson, G. R.; Manzer, L. E. Can. J. Chem. 2000, 78, 920.
21. (c) Reynhardt, J. P. K.; Alper, H. J. Org. Chem. 2003, 68, 8353.
22. (d) Chung, Y.-M.; Rhee, H.-K. C. R. Chim. 2003, 6, 695.
23. Arya, P.; Rao, N. V.; Singkhonrat, J.; Alper, H.; Bourque, S. C.; Manzer, L. E. J. Org. Chem. 2000, 65, 1881.
24. (a) Dahan, A.; Portnoy, M. Macromolecules 2003, 36, 1034.
25. (b) Dahan, A.; Weissberg, A.; Portnoy, M. Chem. Commun. 2003, 1206.
26. Basso, A.; Evans, B.; Pegg, N.; Bradley, M. Chem. Commun. 2001, 697.
27. For use of Mitsunobu coupling in the synthesis of polyether dendrons in solution, see: (a) Zeng, F.; Zimmerman, S. C. J. Am. Chem. Soc. 1996, 118, 5326.
28. (b) Labbe, G.; Forier, B.; Dehaen, W. J. Chem. Soc., Chem. Commun. 1996, 2143.
29. (a) Newman, M. S.; Karnes, H. A. J. Org. Chem. 1966, 31, 3980.
30. (b) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904.
31. Novabiochem-Catalog and Peptide Synthesis Handbook; Novabiochem: Laufelfingen, 1999; p S42.
32. Bar-Nir Ben-Aroya, B.; Portnoy, M. Tetrahedron 2002, 58, 5147.
33. Beletskaya, I. P; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
34. (a) Kivaho, J.; Hanaoka, T.; Kubota, Y.; Sugi, Y. J. Mol. Catal. 1995, 101, 25.
35. (b) Zhao, F.; Bhanage, B. M.; Shirai, M.; Arai, M. Chem.-Eur. J. 2000, 6, 843.
36. (c) Biffis, A.; Zecca, M.; Basato, M. Eur. J. Inorg. Chem. 2001, 1131.
37. (d) Davies, I. W.; Matty, L.; Hughes, D. L.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 10139.
38. (e) Zhao, F.; Shirai, M.; Ikushima, Y.; Arai, M. J. Mol. Catal. A 2002, 180, 211.
39. For rare metal palladium catalysis capable of unactivated bromoarene olefination, see: (a) Kohler, K.; Wagner, M.; Djakovitch, L. Catal. Today 2001, 66, 105 and references therein.
40. (b) Mehnert, C. P.; Ying, T. Y. Chem. Commun. 1997, 2215.
41. (c) Köhler, K.; Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J. Chem.-Eur. J. 2002, 8, 622.
42. For rare examples of supported systems capable of unactivated bromoarene olefination, see: (a) Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101.
43. (b) Schwarz, J.; Bohm, V. P. W.; Gardiner, M. G.; Grosche, M.; Herrman, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Chem.-Eur. J. 2000, 6, 1773.
44. (c) Dell'Anna, M. M.; Mastrorilli, P.; Muscio, F.; Nobile, C. F.; Surranna, G. P. Eur. J. Inorg. Chem. 2002, 1094.
45. (a) Wang, P.-W.; Fox, M. A. J. Org. Chem. 1994, 59, 5358.
46. (b) Villemin, D.; Jaffres, P. A.; Nechab, B.; Courivaud, F. Tetrahedron Lett. 1997, 38, 6581.
47. (c) Riegel, N.; Darcel, C.; Stéphan, O.; Jugé, S. J. Organomet. Chem. 1998, 567, 219.
48. Andersson, C.-M.; Karabelas, K.; Hallberg, A.; Andersson, C. J. Org. Chem. 1985, 50, 3891.
49. Mansour, A.; Portnoy, M. Tetrahedron Lett. 2003, 44, 2195.
50. 2Pd(dba) complexes on dendronized silica, see: Zweni, P. P.; Alper, H. Adv. Synth. Catal. 2004, 346, 849.
51. (a) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
52. (b) Bai, L.; Wang, J. X. Curr. Org. Chem. 2005, 9, 535.
53. (a) Bai, L.; Wang, J. X. Curr. Org. Chem. 2005, 9, 535.
54. (b) Uozumi, Y. Top. Curr. Chem. 2004, 242, 77.
55. (c) Brase, S.; Kirchhoff, J. H.; Kobberling, J. Tetrahedron 2003, 59, 885.
56. (d) Paetzold, E.; Oehme, G.; Fuhrmann, H.; Richter, M.; Eckelt, R.; Pohl, M.-M.; Kosslick, H. Microporous Mesoporous Mater. 2001, 44/45, 517.
57. (e) Kosslick, H.; Monnich, I.; Paetzold, E.; Fuhrmann, H.; Fricke, R.; Müller, D.; Oehme, G. Microporous Mesoporous Mater. 2001, 44/45, 537.
58. Hegedus, L. S. In Organometalics in Organic Synthesis; Schlosser, M., Ed.; Wiley: Chichister, 1994; p 383.
59. Niu, Y. H.; Crooks, R. M. C. R. Chem. 2003, 6, 1049.
60. Yeung, L. K.; Crooks, R. M. Nano Lett. 2001, 1, 14.
61. Cabri, W.; Candian, I. Acc. Chem. Res. 1995, 28, 2.
62. Mansour, A.; Portnoy, M. J. Mol. Catal. A: Chem. 2006, 250, 40.
63. Mansour, A. Supported Catalytic Systems Based on Aminoalcohol-Derived Phosphine Ligands. Ph.D. Thesis. Tel Aviv University, Tel Aviv, 2005.