Polystyrene-supported triphenylarsine reagents and their use in suzuki cross-coupling reactions

Journal of Combinatorial Chemistry

Volumn 6, Issue 6, 2004, Pages 955-960

  Lau, Kelvin Chi Yin ^a   He, Helen Song ^a   Chiu, Pauline ^a   Troy, Patrick H ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ARSINE DERIVATIVE; LIGAND; PALLADIUM; POLYSTYRENE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; RECYCLING; SUZUKI REACTION;

EID: 9344225112     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc049907+     Document Type: Article

References (55)

1. (a) 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. 1 2000, 3815-4195.
2. (b) Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001, 57, 4637-4662.
3. (c) Benaglia, M.; Puglisi, A.; Cozzi, F. Chem. Rev. 2003, 103, 3401-3429.
4. (a) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217-3273.
5. (b) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275-3299.
6. (c) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385-3465.
7. (a) Toy, P. H.; Janda, K. D. Acc. Chem. Res. 2000, 33, 546-554.
8. (b) Dickerson, T. J.; Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325-3343.
9. (c) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345-3383.
10. (a) Toy, P. H.; Janda, K. D. Tetrahedron Lett. 1999, 40, 6329-6332.
11. (b) Garibay, P.; Toy, P. H.; Hoeg-Jensen, T.; Janda, K. D. Synlett 1999, 1438-1440.
12. (c) Toy, P. H.; Reger, T. S.; Janda, K. D. Aldrichimica Acta 2000, 33, 87-93.
13. (d) Toy, P. H.; Reger, T. S.; Garibay, P.; Garno, J. C.; Malikayil, J. A.; Liu, G.-Y.; Janda, K. D. J. Comb. Chem. 2001, 3, 117-124.
14. (e) Choi, M. K. W.; Toy, P. H. Tetrahedron 2004, 60, 2903-2907.
15. Toy, P. H.; Reger, T. S.; Janda, K. D. Org. Lett. 2000, 2, 2205-2207.
16. Kan, J. T. W.; Toy, P. H. Tetrahedron Lett. 2004, 45, 6357-6359.
17. Choi, M. K. W.; Toy, P. H. Tetrahedron 2004, 60, 2875-2879.
18. Choi, M. K. W.; Toy, P. H. Tetrahedron 2003, 59, 7171-7176.
19. Choi, M. K. W.; He, H. S.; Toy, P. H. J. Org. Chem. 2003, 68, 9831-9834.
20. Huang, Y.-Z.; Shi, L.-L.; Zhou, Z.-L. Triphenylarsine. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A, Ed.; Wiley: 1995; pp 5339-5342.
21. (a) Huang, Y. Z.; Shen, Y. C. Adv. Organomet. Chem. 1982, 20, 115-157.
22. (b) Lloyd, D.; Gosney, I.; Ormiston, R. A. Chem. Soc. Rev. 1987, 16, 45-74.
23. (c) Moorhoff, C. M. Recent Res. Devel. Org. Chem. 2000, 4, 239-259.
24. (d) Aggarwal, V. K.; Patel, M.; Studley, J. Chem. Commun. 2002, 1514-1515.
25. (e) Goddard, J.-P.; Lixon, P.; Le Gall, T.; Mioskowski, C. J. Am. Chem. Soc. 2003, 125, 9242-9243.
26. (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
27. (b) Faust, R.; Göbelt, B. J. Prakt. Chem. 1998, 340, 90-93.
28. Leadbeater, N. E. Curr. Med. Chem. 2002, 9, 2147-2171.
29. For reports of polystyrene-supported triphenylarsine, see: (a) Smith, C. P.; Temme, G. H. J. Org. Chem. 1983, 48, 4681-4685. (b) Steiner, U. B.; Caseri, W. R.; Suter, U. W. Langmuir 1998, 14, 347-351.
30. For reports of polystyrene-supported triphenylarsine, see: (a) Smith, C. P.; Temme, G. H. J. Org. Chem. 1983, 48, 4681-4685. (b) Steiner, U. B.; Caseri, W. R.; Suter, U. W. Langmuir 1998, 14, 347-351.
31. 0 catalyst, see: Cai, M.; Huang, Y.; Zhao, H.; Song, C. React. Funct. Polym. 2004, 59, 81-86.
32. (a) Lim, A. R.; Kim, J. H.; Novak, B. M. Polymer 2000, 41, 2431-2438.
33. (b) Lim, A. R.; Chang, J. H.; Kim, J. H.; Novak, B. M. Solid State Commun. 2000, 115, 23-28.
34. Arshady, R. J. Macromol. Sci. Rev. Macromol. Chem. Phys. 1992, C32, 101-132.
35. van Vliet, M. C. A.; Arends, I. W. C. E.; Sheldon, R. A. Tetrahedron Lett. 1999, 40, 5239-5242.
36. (a) Arshady, R.; Ledwith, A. React. Polym. 1983, 1, 159-174.
37. (b) Arshady, R. Chim. Ind. 1988, 70, 70-75.
38. (c) Arshady, R. Colloid Polym. Sci. 1992, 270, 717-732.
39. (d) Sherrington, D. C. Chem. Commun. 1998, 2275-2286.
40. JandaJel is a registered trademark of the Aldrich Chemical Co.
41. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
42. (a) For the use of a polymer-supported benzyldiphenylphosphine as a palladium ligand in Suzuki reactions, see: Fenger, I.; Le Drian, C. Tetrahedron Lett. 1998, 39, 4287-4290.
43. (b) For the use of a polymer-supported biphenyldicylohexylphosphine as a palladium ligand in Suzuki reactions, see: Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820-3827.
44. (c) For the use of an amphiphilic polymer-supported palladium catalyst in Suzuki reactions, see: Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S. Org. Lett. 2002, 4, 3371-3374.
45. (d) For the use of a polymer-supported ferrocenylmethylphosphine as a palladium ligand in Suzuki reactions, see: Hu, Q. S.; Lu, Y.; Tang, Z. Y.; Yu, H. B. J. Am. Chem. Soc. 2003, 125, 2856-2857.
46. (e) For the use of heterogeneous palladium on carbon in Suzuki reactions, see: Tagata, T.; Nishida, M. J. Org. Chem. 2003, 68, 9412-9415 and references therein.
47. (f) For a report of an anthracene-tagged phosphine as a palladium ligand that can be removed by reaction with a polymeric reagent in Suzuki reactions, see: Lan, P.; Berta, D.; Porco, J. A., Jr.; South, M. S.; Parlow, J. J. J. Org. Chem. 2003, 68, 9678-9686.
48. (g) For a report of silica-supported oxime carbapalladacycle catalyzed Suzuki reactions, see: Baleizao, C.; Corma, A.; Garcia, H.; Leyva, A. J. Org. Chem. 2004, 69, 439-446.
49. (h) For the use of a silica sol - gel entrapped Pd-(II) catalyst in Heck reactions, see: Hamza, K.; Abu-Reziq, R.; Avnir, D.; Blum, J. Org. Lett. 2004, 6, 925-927.
50. (i) For the use of polymer-incarcerated palladium as a catalyst in Suzuki reactions, see: Okamoto, K.; Akiyama, R.; Kobayashi, S. Org. Lett. 2004, 6, 1987-1990.
51. (j) For the use of a palladium - Y-zeolite catalyst in Suzuki reactions, see: Artok, L.; Bulut, H. Tetrahedron Lett. 2004, 45, 3881-3884.
52. Ruel, F. S.; Braun, M. P.; Johnson, C. R. Org. Synth. 1998, 75, 69-77.
53. Grasa, G. A.; Hillier, A. C.; Nolan, S. P. Org. Lett. 2001, 3, 1077-1080.
54. Kobayashi, S.; Akiyama, R. Chem. Commun. 2003, 449-460 and references therein.
55. For details of the reaction setup used, see: Wilson, M. E.; Paech, K.; Zhou, W. J.; Kurth, M. J. J. Org. Chem. 1998, 63, 5094-5099.