Hiyama reaction of aryl bromides with arylsiloxanes catalyzed by a reusable palladium(II)/cationic bipyridyl system in water

Tetrahedron

Volumn 64, Issue 35, 2008, Pages 8164-8168

  Chen, Shao Nung ^a   Wu, Wei Yi ^a   Tsai, Fu Yu ^a  

^a NATIONAL TAIPEI UNIVERSITY OF TECHNOLOGY   (Taiwan)

Author keywords

Biaryls; Cross coupling; Hiyama reaction; Reusable; Water soluble catalyst

Indexed keywords

BIPYRIDINE DERIVATIVE; BROMINE DERIVATIVE; CATION; PALLADIUM; SILOXANE; SODIUM HYDROXIDE; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; EXTRACTION; HIYAMA REACTION; PRIORITY JOURNAL; REACTION OPTIMIZATION; TEMPERATURE;

EID: 47049083399     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.050     Document Type: Article

References (83)

1. In: Diederich F., and Stang P.J. (Eds). Metal-Catalyzed Cross-coupling Reactions (1998), Wiley-VCH, New York, NY
2. In: Miyaura N. (Ed). Cross-coupling Reactions: A Practical Guide. Topics in Current Chemistry Series Vol. 219 (2002), Springer, New York, NY
3. de Meijere A., and Diederich F. Metal-Catalyzed Cross-coupling Reactions. 2nd ed. (2004), Wiley-VCH, Weinheim
4. Beller M., and Bolm C. Transition Metals for Organic Synthesis; Building Block and Fine Chemicals. 2nd Ed. (2004), Wiley-VCH, Weinheim
5. Yin L., and Liebscher J. Chem. Rev. 107 (2007) 133
6. Astruc D. Inorg. Chem. 46 (2007) 1884
7. Liu S., and Xiao J. J. Mol. Catal. A: Chem. 270 (2007) 1
8. Barnard C. Platinum Met. Rev. 52 (2008) 38
9. For recent reviews, see:
10. Stille J.K. Angew. Chem., Int. Ed. Engl. 25 (1986) 508
11. Kosugi M., and Fugami K. J. Organomet. Chem. 653 (2002) 50
12. Espinet P., and Echavarren A.M. Angew. Chem., Int. Ed 43 (2004) 4704
13. Wang D.-P., Zhang X.-D., Liang Y., and Li J.-H. Chin. J. Org. Chem. 26 (2006) 19
14. De Souza M.V.N. Curr. Org. Synth. 3 (2006) 313
15. For recent reviews, see:
16. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
17. Stanforth S.P. Tetrahedron 54 (1998) 263
18. Suzuki A. J. Organomet. Chem. 576 (1999) 147
19. Suzuki A. J. Organomet. Chem. 653 (2002) 83
20. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis (2002), John Wiley and Sons, New York, NY
21. In: Cornils B., and Herrmann W.A. (Eds). Applied Homogeneous Catalysis with Organometallic Compounds (2002), Wiley-VCH, Weinheim
22. Phan N.T.S., Van Der Sluys M., and Jones C.W. Adv. Synth. Catal. 348 (2006) 609
23. For recent reviews, see:
24. Hiyama T. J. Organomet. Chem. 653 (2002) 58
25. Denmark S.E., and Sweis R.F. Acc. Chem. Res. 35 (2002) 835
26. Denmark S.E., and Ober M.H. Aldrichimica Acta 36 (2003) 75
27. Handy C.J., Manoso A.S., McElroy W.T., Seganish W.M., and DeShong P. Tetrahedron 61 (2005) 12201 and references therein
28. Hatanaka Y., and Hiyama T. J. Org. Chem. 53 (1988) 918
29. Hatanaka Y., Fukushima S., and Hiyama T. Chem. Lett. (1989) 1711
30. Gouda K., Hagiwara E., Hatanaka Y., and Hiyama T. J. Org. Chem. 61 (1996) 7232
31. Shibata K., Miyazawa K., and Goto Y. Chem. Commun. (1997) 1309
32. Mowery M.E., and DeShong P. J. Org. Chem. 64 (1999) 1684
33. Mowery M.E., and DeShong P. Org. Lett. 1 (1999) 2137
34. Mowery M.E., and DeShong P.J. J. Org. Chem. 64 (1999) 3266
35. Lee H.M., and Nolan S.P. Org. Lett. 2 (2000) 2053
36. Correia R., and DeShong P. J. Org. Chem. 66 (2001) 7159
37. Denmark S.E., and Sweis R.F. Org. Lett. 4 (2002) 3771
38. Riggleman S., and DeShong P. J. Org. Chem. 68 (2003) 8106
39. McElroy W.T., and DeShong P. Org. Lett. 5 (2003) 4779
40. Wolf C., Lerebours R., and Tanzini E.H. Synthesis (2003) 2069
41. Seganish W.M., and DeShong P. J. Org. Chem. 69 (2004) 1137
42. Seganish W.M., and DeShong P. J. Org. Chem. 69 (2004) 6790
43. Sahoo A.K., Oda T., Nakao Y., and Hiyama T. Adv. Synth. Catal. 346 (2004) 1715
44. Li J.-H., Deng C.-L., Liu W.-J., and Xie Y.-X. Synthesis (2005) 3039
45. Pierrat P., Gros P., and Fort Y. Org. Lett. 7 (2005) 697
46. Jayanth E.T., Jaganmohan M., and Cheng C.-H. Org. Lett. 7 (2005) 2921
47. Murata M., Yoshida S., Nirei S., Watanabe S., and Masuda Y. Synlett (2006) 118
48. Mino T., Shirae Y., Saito T., Sakamoyo M., and Fujita T. J. Org. Chem. 71 (2006) 9499
49. Ju J., Nam H., Jung H.M., and Lee S. Tetrahedron Lett. 47 (2006) 8673
50. Prukała W., Marciniec B., Majchrzak M., and Kubicki M. Tetrahedron 63 (2007) 1107
51. Hagiwara E., Gouda K., Hatanaka Y., and Hiyama T. Tetrahedron Lett. 38 (1997) 439
52. Murata M., Shimazaki R., Watanabe S., and Masuda Y. Synthesis (2001) 2231
53. Huang T., and Li J.C. Tetrahedron Lett. 43 (2002) 403
54. Wolf C., and Lerebours R. Org. Lett. 6 (2004) 1147
55. Lerebours R., and Wolf C. Synthesis (2005) 2287
56. Gordillo A., de Jesús E., and López-Mardomingo C. Org. Lett. 8 (2006) 3517
57. Alacid E., and Nájera C. Adv. Synth. Catal. 348 (2006) 2085
58. Gordillo A., de Jesús E., and López-Mardomingo C. Chem. Commun. (2007) 4056
59. Srimani D., Sawoo S., and Sarkar A. Org. Lett. 9 (2007) 3639
60. Alacid E., and Nájera C. Adv. Synth. Catal. 348 (2006) 945
61. Shi S., and Zhang Y. J. Org. Chem. 72 (2007) 5927
62. Wu W.-Y., Chen S.-N., and Tsai F.-Y. Tetrahedron Lett. 47 (2006) 9267
63. Wang Y.-H., and Tsai F.-Y. Chem. Lett. (2007) 1492
64. Manoso A.S., Ahn C., Soheili A., Handy C.J., Correia R., Seganish W.M., and DeShong P. J. Org. Chem. 69 (2004) 8305
65. Oki A.R., and Morgan R.J. Synth. Commun. 25 (1995) 4093
66. Will G., Boschloo G., Rao S.N., and Fitzmaurice D. J. Phys. Chem. B 103 (1999) 8067
67. Tsai F.-Y., Lin B.-N., Chen M.-J., Mou C.-Y., and Liu S.-T. Tetrahedron 63 (2007) 4304
68. Nájera C., Gil-Moltó J., Karlström S., and Falvello L.R. Org. Lett. 5 (2003) 1451
69. Mino T., Shirae Y., Sakamoto M., and Fujita T. J. Org. Chem. 70 (2005) 2191
70. Leadbeater N.E., and Resouly S.M. Tetrahedron 55 (1999) 11889
71. Ueura K., Satoh T., and Miura M. Org. Lett. 7 (2005) 2229
72. Wolfe J.P., Singer R.A., Yang B.H., and Buchwald S.L. J. Am. Chem. Soc. 121 (1999) 9550
73. Nakamichi N., Kawabata H., and Hayashi M. J. Org. Chem. 68 (2003) 8272
74. Demark S., and Ober M.H. Org. Lett. 5 (2003) 1357
75. Byron D.J., Gray G.W., and Wilson R.C. J. Chem. Soc. C (1966) 840
76. Lu J., Tao Y., D'iorio M., Li Y., Ding J., and Day M. Macromolecules 37 (2004) 2442
77. Farina V., Krishnan B., Marshall D.R., and Roth G.P. J. Org. Chem. 58 (1993) 5434
78. Mutule I., and Suna E. Tetrahedron 61 (2005) 11168
79. Hagio H., Sugiura M., and Kobayashi S. Org. Lett. 8 (2006) 375
80. de la Mare P.B.D., Hall D.M., Harris M.M., Hassan M., Johnson E.A., and Klassen N.V. J. Chem. Soc. (1962) 3784
81. Littke A.F., Dai C., and Fu G.C. J. Am. Chem. Soc. 122 (2000) 4020
82. Ackermann L., and Althammer A. Org. Lett. 8 (2006) 3457
83. Tao B., and Boykin D.W. J. Org. Chem. 69 (2004) 4330