Recyclable and reusable Pd(OAc)2/DABCO/PEG-400 system for Suzuki-Miyaura cross-coupling reaction

Journal of Organic Chemistry

Volumn 70, Issue 14, 2005, Pages 5409-5412

  Li, Jin Heng ^a   Liu, Wen Jie ^a   Xie, Ye Xiang ^a  

^a HUNAN NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; CATALYSIS; INORGANIC ACIDS; IODINE;

ARYL HALIDES; ARYLBORONIC ACIDS; CROSS-COUPLING REACTIONS; TURNOVER NUMBER (TON);

RECYCLING;

1 IODO 4 NITROBENZENE; 1,4 DIAZABICYCLO[2.2.2]OCTANE; ACETIC ACID DERIVATIVE; BENZENEBORONIC ACID; BORONIC ACID DERIVATIVE; BROMIDE; HALIDE; IODIDE; MACROGOL 400; NITROBENZENE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL PARAMETERS; CHEMICAL REACTION KINETICS; CROSS COUPLING REACTION; RECYCLING; SUZUKI MIYAURA REACTION; TURNOVER NUMBER;

EID: 22144490863     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050353m     Document Type: Article

References (68)

1. Bringmann, G.; Gunther, C.; Ochse, M.; Schupp, O.; Tasler, S. In Progress in the Chemistry of Organic Natural Products; Herz, W., Falk, H., Kirby, G. W., Moore, R. E., Eds.; Springer: New York, 2001; Vol. 82, pp 1-293.
2. (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977.
3. (b) Hegedus, L. S. In Organometallics in Synthesis; Schlosser, M., Ed.; J. Wiley & Sons: Chichester, 2002; p1123.
4. (c) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002.
5. For selected Ullmann coupling reactions, see: (a) Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312.
6. (b) Li, J.-H.; Xie, Y.-X.; Yin, D.-L. J. Org. Chem. 2003, 68, 9867 and reference cited therein.
7. For reviews, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
8. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions, Wiley-VCH: Weinheim, 1998.
9. (c) Miyaura, N. Cross-Coupling Reaction, Springer: Berlin, 2002.
10. (d) Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 2419.
11. (e) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127.
12. For recently selected papers on phosphine-palladium catalysts, see: (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
13. (b) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
14. (c) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem., Soc. 2000, 122, 4020.
15. (d) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem., Int. Ed. 2002, 41, 4120.
16. (e) Feuerstein, M.; Berthiol, F.; Doucet, H.; Santelli, M. Synlett 2002, 1807.
17. (f) Mori, K.; Yamaguchi, K.; Kara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2002, 124, 11572.
18. (g) Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162.
19. (h) Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.
20. (i) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
21. (j) Kwong, F. Y.; Lam, W. H.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Chem. Commun. 2004, 1922.
22. (k) Kwong, F. Y.; Chan, K. S.; Yeung, C. H.; Chan, A. S. C. Chem. Commun. 2004, 2336.
23. (l) Brenstrum, T.; Gerristma, D. A.; Adjabeng, G. M.; Frampton, C. S.; Britten, J.; Robertson, A. J.; McNulty, J.; Capretta, A. J. Org. Chem. 2004, 69, 7635.
24. (m) Baillie, C.; Zhang, L.; Xiao, J. J. Org. Chem. 2004, 69, 7779.
25. (n) DeVasher, R. B.; Moore, L. R.; Shaughnessy, K. H. J. Org. Chem. 2004, 69, 7919.
26. (o) Mukherjee, A.; Sarkar, A. Tetrahedron Lett. 2004, 45, 9525.
27. (p) Zhang, W.; Shi, M. Tetrahedron Lett. 2004, 45, 8921.
28. (q) Peyroux, E.; Berthiol, F.; Doucet, H. Santelli, M. Eur. J. Org. Chem. 2004, 1075.
29. (r) Willis, M. C.; Powell, L. H.; Claverie, C. K. Angew. Chem., Int. Ed. 2004, 43, 1249.
30. (s) Wang, A.-E.; Zhang, J.; Xie, J.-H.; Li, K.; Zhou, Q.-L. Adv. Synth. Catal. 2004, 346, 595.
31. (t) Berthiol, F.; Kondolff, I.; Doucet, H.; Santelli, M. J. Organomet. Chem. 2004, 689, 2786.
32. (u) Okamoto, K.; Akiyama, R.; Kobayashi, S. Org. Lett. 2004, 6, 1987.
33. (v) Barder, T. E.; Buchwald, S. L. Org. Lett. 2004, 6, 2649.
34. (w) Colacot, T. J.; Shea, H. A. Org. Lett. 2004, 6, 3731.
35. (x) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871.
36. (y) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
37. For recent reviews on N-heterocyclic carbene-palladium catalysts, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
38. (b) Yong, B. S.; Nolan, S. P. Chemtracts: Org. Chem. 2003, 205.
39. For a representative paper on thiourea-palladium catalyst, see: Dai, M.; Liang, B.; Wang, C.; Chen, J.; Yang, Z. Org. Lett. 2004, 6, 221.
40. For a representative paper on C,N-based 2-aryl-2-oxazolines-palladium catalyst, see: Tao, B.; Boykin, D. W. Tetrahedron Lett. 2002, 43, 4955.
41. For selected representative papers on aryloximes-palladium catalyst, see: (a) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Org. Lett. 2000, 2, 1823.
42. (b) Botella, L.; Nájera, C. Angew. Chem., Int. Ed. 2002, 41, 179.
43. For a paper on arylimines-palladium catalyst, see: Bedford, R. B.; Cazin, C. S. Chem. Commun. 2001, 1540.
44. For recent representative papers on diazabutadiene-palladium catalysts, see: (a) Grasa, G. A.; Hillier, A. C.; Nolan, S. P. Org. Lett. 2001, 3, 1077.
45. (b) Palencia, H.; Garcia-Jimenez, F.; Takacs, J. M. Tetrahedron Lett. 2004, 45, 3849.
46. For the representative papers on amine-palladium catalysts, see: (a) Tao, B.; Boykin, D. W. Tetrahedron Lett. 2003, 44, 7993.
47. (b) Tao, B.; Boykin, D. W. J. Org. Chem. 2004, 69, 4330.
48. (c) Li, J.-H.; Liu, W.-J. Org. Lett. 2004, 6, 2809.
49. For recent representative papers on other phosphine-free palladium catalysts, see: (a) Alonso, D. A.; Nájera, C.; Pacheco, M. C. J. Org. Chem. 2002, 67, 5588 and reference cited therein.
50. (b) de Vries, A. H. M. Mulders, J. M. C. A.; Mommers, J. H. M.; Henderickx, H. J. W.; de Vries, J. G. Org. Lett. 2003, 5, 3285 and references therein.
51. For selected papers on recyclable palladium catalysts for Suzuki-Miyaura cross-coupling reaction: (a) Kaneda, K.; Terasawa, M.; Imanaka, T.; Teranishi, S. Fundam. Res. Homogeneous Catal. 1973, 3, 671.
52. (b) Terasawa, M.; Kane, K.; Imanaka, T.; Teranishi, S. J. Organomet. Chem. 1978, 162, 403.
53. (c) Andersson, C.-M.; K. Karabelas, A. Hallberg, J. Org. Chem. 1985, 50, 3891.
54. (d) Zhang, Z. Y.; Hu, H. W.; Kao, T. Y. React. Polym. Ion. Exch. Sorbents 1988, 9, 249.
55. (e) Zhang, Z. Y.; Pan, Y.; Hu, H. W.; Kao, T. Y. Synth. Commun. 1990, 20, 3563.
56. (f) Jang, S. B. Tetrahedron Lett. 1997, 38, 4421.
57. (g) Bergbreiter, D. E.; L. Osburn, P.; Liu, Y. S. J. Am. Chem. Soc. 1999, 121, 9531.
58. (h) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243.
59. (i) Akiyama, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2001, 40, 3469.
60. (j) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
61. (k) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057.
62. (l) Phan, N. T. S.; Brown, D. H.; Styring, P. Tetrahedron Lett. 2004, 45, 7915.
63. (a) Pignolet, L. H., Ed.; Homogeneous Catalysis with Metal Phosphine Complexes; Plenum; New York, 1983.
64. (b) Parshall, G. W.; Ittel, S. Homogeneous Catalysis; Wiley and Sons: New York, 1992.
65. (c) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science: Mill Vallley, CA, 1987.
66. For a selected representative paper on PEG as the media for the other cross-coupling reactions, see: Chandrasehar, S.; Narsihmulu, C.; Sultana, S. S.; Reddy, N. R. Org. Lett. 2002, 4, 4399.
67. For the representative papers on TBAB-promoted the cross-coupling reactions, see: (a) Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002 4, 3031.
68. (b) Yang, D.; Chen, Y.-C.; Zhu, N.-Y. Org. Lett. 2004, 6, 1557 and references therein.