Nickel(0)/tetra-n-butylammonium bromide (TBAB) catalyzed Suzuki-Miyaura reaction

Synthesis

Volumn , Issue 9, 2006, Pages 1465-1469

  You, Erli ^a   Li, Pinhua ^a   Wang, Lei ^a,b  

^a HUAIBEI NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Nickel(0) metal colloids; Suzuki Miyaura reaction; Tetra n butylammonium bromide (TBAB)

Indexed keywords

AMMONIUM COMPOUNDS; CARBOXYLIC ACIDS; CATALYSIS; COLLOIDS; ETHANOL; REACTION KINETICS; SODIUM CHLORIDE; SOLVENTS;

NICKEL(0) METAL COLLOIDS; PHOSPHINE-FREE REACTIONS; SUZUKI-MIYAURA REACTION; TETRA-N-BUTYLAMMONIUM BROMIDE (TBAB);

BROMINE COMPOUNDS;

ALCOHOL; BICARBONATE; BORONIC ACID DERIVATIVE; BROMINE DERIVATIVE; CHLORIDE; IODINE DERIVATIVE; NICKEL; ORGANOBORONIC ACID; QUATERNARY AMMONIUM DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; COLLOID; RECYCLING; SUZUKI REACTION;

EID: 33646578818     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926424     Document Type: Article

References (62)

1. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
2. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
3. (c) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
4. Hajduk, P. J.; Bures, M.; Praestgaard, J.; Fesik, S. W. J. Med. Chem. 2000, 43, 3443.
5. (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
6. (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; VCH: Weinheim, 1998, 49-97.
7. (c) Alo, B. I.; Kandil, A.; Patil, P. A.; Sharp, M. J.; Siddiqui, M. A.; Snieckus, V.; Josephy, P. D. J. Org. Chem. 1991, 56, 3763.
8. (d) Wallow, T. I.; Novak, B. M. J. Org. Chem. 1994, 59, 5034.
9. (e) Genet, J. P.; Linquist, A.; Blart, E.; Mouries, V.; Savignac, M. Tetrahedron Lett. 1995, 36, 1443.
10. (f) Genet, J. P.; Savignac, M. J. Organomet. Chem. 1999, 576, 305.
11. (a) Marck, G.; Villiger, A.; Buchecker, R. Tetrahedron Lett. 1994, 35, 3277.
12. (b) LeBlond, C. R.; Andrews, A. T.; Sowa, J. R. Jr.; Sun, Y. Org. Lett. 2001, 3, 1555.
13. (c) Tagata, T.; Nishida, M. J. Org. Chem. 2003, 68, 9412.
14. (d) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721.
15. (a) Kabalka, G. W.; Pagni, R. M.; Hair, C. M. Org. Lett. 1999, 1, 1423.
16. (b) Kabalka, G. W.; Namboodiri, V.; Wang, L. Chem. Commun. 2001, 775.
17. (c) Kabalka, G. W.; Wang, L.; Pagni, R. M.; Hair, C. M.; Namboodiri, V. Synthesis 2003, 217.
18. Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127.
19. (a) Reetz, M. T.; Helbig, W.; Quaiser, S. A.; Stimming, U.; Breuer, N.; Vogel, R. Science 1995, 267, 367.
20. (b) Reetz, M. T.; Winter, M.; Breinbauer, R.; Thurn-Albrecht, T.; Vogel, W. Chem. Eur. J. 2001, 7, 1084.
21. (c) Reetz, M. T.; Westermann, E. Angew. Chem. Int. Ed. 2000, 39, 165.
22. (d) Reetz, M. T.; Westermann, E.; Lohmer, R.; Lohmer, G. Tetrahedron Lett. 1998, 39, 8449.
23. (e) Reetz, M. T.; Breinbauer, R.; Wanninger, K. Tetrahedron Lett. 1996, 37, 4499.
24. (f) Reetz, M. T.; Vries, J. G. Chem. Commun. 2004, 1559.
25. Bradley, J. S.; Millar, J. M.; Hill, E. W. J. Am. Chem. Soc. 1991, 113, 4016.
26. (a) Narayanan, R.; El-Sayed, M. A. J. Am. Chem. Soc. 2003, 125, 8340.
27. (b) Li, Y.; Hong, X. M.; Collard, D. M.; El-Sayed, M. A. Org. Lett. 2000, 2, 2385.
28. (a) Botella, L.; Nájera, C. Angew. Chem. Int. Ed. 2002, 41, 179.
29. (b) Botella, L.; Nájera, C. J. Organomet. Chem. 2002, 663, 46.
30. Zou, Y.; Wang, Q.; Tao, F.; Ding, Z. Chin. J. Chem. 2004, 22, 215.
31. Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 5660.
32. (a) Saito, S.; Oh-tani, S.; Miyaura, N. J. Org. Chem. 1997, 62, 8024.
33. (b) Percec, V.; Bae, J.; Hill, D. H. J. Org. Chem. 1995, 60, 1060.
34. (c) Indolese, A. F. Tetrahedron Lett. 1997, 38, 3513.
35. (a) Lipshutz, B. H.; Frieman, B. Tetrahedron 2004, 60, 1309.
36. (b) Lipshutz, B. H.; Sclafani, J. A.; Blomgren, P. A. Tetrahedron 2000, 56, 2139.
37. (c) Lipshutz, B. H. Adv. Synth. Catal. 2001, 343, 313 and references cited therein.
38. (d) Lipshutz, B. H.; Tasler, S. Adv. Synth. Catal. 2001, 343, 327.
39. (e) Tang, Z.; Hu, Q. J. Am. Chem. Soc. 2004, 126, 3058.
40. (f) Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222.
41. Zim, D.; Lando, V. R.; Dupont, J.; Monteiro, A. L. Org. Lett. 2001, 3, 3049.
42. Park, J.; Kang, E.; Son, S. U.; Park, H. M.; Lee, M. K.; Kim, J.; Kim, K. W.; Noh, H.; Park, J.; Bae, C. J.; Park, J.; Hyeon, T. Adv. Mater. 2005, 17, 429.
43. (a) Zim, D.; Monteiro, A. L. Tetrahedron Lett. 2002, 43, 4009.
44. (b) Leadbeater, N. E.; Resouly, S. M. Tetrahedron 1999, 55, 11889.
45. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 1340.
46. (a) Lipshutz, B. H.; Tasler, S.; Chrisman, W.; Spliethoff, B.; Tesche, B. J. Org. Chem. 2003, 68, 1177.
47. (b) Tasler, S.; Lipshutz, B. H. J. Org. Chem. 2003, 68, 1190.
48. (a) Brown, H. C.; Bhat, N. G.; Somayaji, V. Organometallics 1992, 11, 652.
49. (b) Brown, H. C.; Scouten, C. G.; Liotta, R. J. Am. Chem. Soc. 1979, 101, 96.
50. Newman, M. S.; Eberwein, J. A. J. Org. Chem. 1964, 29, 2516.
51. Cho, C.; Sun, M.; Seo, Y.; Kim, C.; Park, K. J. Org. Chem. 2005, 70, 1482.
52. Hermann, E. C.; Hoyer, G.-A.; Kelm, J. Spectrochim. Acta, Part A 1982, 38, 1057.
53. Brune, H.-A.; Hess, R.; Schmidtberg, G. Z. Naturforsch., B: Anorg. Chem. Org. Chem. 1984, 39, 1772.
54. Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797.
55. Hendrickson, J. B.; Wolf, W. A. J. Org. Chem. 1968, 33, 3610.
56. Patrick, T. B.; Willaredt, R. P.; DeGonia, D. J. J. Org. Chem. 1985, 50, 2232.
57. Dewar, M. J. S.; Hart, L. S. Tetrahedron 1970, 26, 1001.
58. Klemm, L. H.; Stevens, M. P.; Tran, L. K.; Sheley, J. J. Heterocycl. Chem. 1988, 25, 1111.
59. Miles, P.; Suschitzky, H. Tetrahedron 1963, 19, 385.
60. Eisch, J. J.; Hallenbeck, L. E.; Han, K. I. J. Am. Chem. Soc. 1968, 108, 7763.
61. Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170.
62. Hassan, J.; Hathroubi, C.; Gozzi, C.; Lemaire, M. Tetrahedron 2001, 57, 7845.