Highly efficient reusable polymer-supported Pd catalysts of general use for the Suzuki reaction

Tetrahedron

Volumn 66, Issue 3, 2010, Pages 765-772

  Schweizer, Stéphane ^a   Becht, Jean Michel ^a   Le Drian, Claude ^a  

^a UNIVERSITÉ DE HAUTE ALSACE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; PHOSPHINE DERIVATIVE; POLYMER; POLYSTYRENE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; PRIORITY JOURNAL; SUZUKI REACTION; SYNTHESIS;

EID: 71949086774     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.11.050     Document Type: Article

References (84)

1. Diederich F., and Stang P.J. Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH, Weinheim
2. Tsuji J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century (2004), John Wiley, New York, NY
3. Miyaura N., Yamada K., and Suzuki A. Tetrahedron Lett. 36 (1979) 3437
4. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
5. Kotha S., Lahiri K., and Kashinath D. Tetrahedron 58 (2002) 9633
6. Hassan J., Sévignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359
7. Other powerful transition metal-catalyzed synthetic methods for the preparation of biaryls are available.
8. For Cu-catalyzed cross-coupling reactions see:. Fanta P.E. Synthesis (1974) 9
9. For Ni-catalyzed cross-coupling reactions see:. Lee C.-C., Ke W.-C., Chan K.T., Lai C.-L., Hu C.-H., and Lee H.M. Chem.-Eur. J. 13 (2007) 582 and references therein
10. For C-H activation reactions see:. Alberico D., Scott M.E., and Lautens M. Chem. Rev. 107 (2007) 174
11. For decarboxylative Pd-catalyzed reactions see:. Becht J.-M., Catala C., Le Drian C., and Wagner A. Org. Lett. 9 (2007) 1781 and references therein
12. Becht J.-M., and Le Drian C. Org. Lett. 10 (2008) 3161
13. Lloyd-Williams P., and Giralt E. Chem. Soc. Rev. 30 (2001) 145 and references therein
14. Pu L. Chem. Rev. 98 (1998) 2405 and references therein
15. De Vos D.E., Dams M., Sels B.F., and Jacobs P.A. Chem. Rev. 102 (2002) 3615
16. Choudary B.M., Madhi S., Chowdari N.S., Kantam M.L., and Sreedhar B. J. Am. Chem. Soc. 124 (2002) 14127
17. Mori K., Yamaguchi T., Hara T., Mizukagi T., Ebitani K., and Kaneda K. J. Am. Chem. Soc. 124 (2002) 11572
18. Bulut H., Artok L., and Yilmaz S. Tetrahedron Lett. 44 (2003) 289
19. Shimizu K.I., Kan-no T., Kodama T., Hagiwara H., and Kitayama Y. Tetrahedron Lett. 43 (2002) 5653
20. Baleizao C., Corma A., Garcia H., and Leyva A. Chem. Commun. (2003) 606
21. Sayah R., Glegola K., Framery E., and Dufaud V. Adv. Synth. Catal. 349 (2007) 373
22. Trilla M., Pleixats R., Wong Chi Man M., Bied C., and Moreau J.J.E. Adv. Synth. Catal. 350 (2008) 577
23. Leadbeater N.E., and Marco M. Chem. Rev. 102 (2002) 3217
24. McNamara C.A., Dixon M.J., and Bradley M. Chem. Rev. 102 (2002) 3275
25. Dickerson T.J., Reed N.N., and Janda K.D. Chem. Rev. 102 (2002) 3325
26. Bergbreiter D.E. Chem. Rev. 102 (2002) 3345
27. Lu J., and Toy P.H. Chem. Rev. 109 (2009) 815
28. Ramarao C., Ley S.V., Smith S.C., Shirley I.M., and DeAlmeida N. Chem. Commun. (2002) 1132
29. Ley S.V., Ramarao C., Gordon R.S., Holmes A.B., Morrison A.J., McConvey I.F., Shirley I.M., Smith S.C., and Smith M.D. Chem. Commun. (2002) 1134
30. Trzeciak A.M., Mieczyńska E., Ziólkowski W., Bukowska A., Noworól J., and Okal J. New J. Chem. 32 (2008) 1124
31. Akiyama R., and Kobayashi S. J. Am. Chem. Soc. 125 (2003) 3412
32. Okamoto K., Akiyama R., and Kobayashi S. Org. Lett. 6 (2004) 1987
33. Nishio R., Sugiura M., and Kobayashi S. Org. Lett. 7 (2005) 4831
34. Hagio H., Sugiura M., and Kobayashi S. Org. Lett. 8 (2006) 375
35. Akiyama R., and Kobayashi S. Chem. Rev. 109 (2009) 594
36. Kim J.-H., Kim J.-W., Shokouhimehr M., and Lee Y.-S. J. Org. Chem. 70 (2005) 6714
37. Byun J.-W., and Lee Y.-S. Tetrahedron Lett. 45 (2004) 1837
38. Shokouhimehr M., Kim J.-H., and Lee Y.-S. Synlett 4 (2006) 618
39. Andersson C.-M., Karabelas K., and Hallberg A. J. Org. Chem. 50 (1985) 3891
40. Riegel N., Darcel C., Stéphan O., and Jugé S. J. Organomet. Chem. 567 (1998) 219
41. Uozomi Y., Danjo H., and Hayashi T. J. Org. Chem. 64 (1999) 3384
42. Dahan A., and Portnoy M. Org. Lett. 5 (2003) 1197
43. Uozomi Y., and Kimura T. Synlett (2002) 2045
44. Yamada Y.M., Takeda K., Takahashi H., and Ikegami S. J. Org. Chem. 68 (2003) 7733
45. Kang T., Feng Q., and Luo M. Synlett 15 (2005) 2305
46. Guinó M., and Hii K.K. Chem. Soc. Rev. 36 (2007) 608
47. Lombardo M., Chiarucci M., and Trombini C. Green Chem. 11 (2009) 574
48. Fenger I., and Le Drian C. Tetrahedron Lett. 39 (1998) 4287
49. Schweizer S., Becht J.-M., and Le Drian C. Adv. Synth. Catal. 349 (2007) 1150
50. Schweizer S., Becht J.-M., and Le Drian C. Org. Lett. 9 (2007) 3777
51. Walker S.D., Barder T.E., Martinelli J.R., and Buchwald S.L. Angew. Chem., Int. Ed. 43 (2004) 1871
52. Barder T.E., Walker S.D., Martinelli J.R., and Buchwald S.L. J. Am. Chem. Soc. 127 (2005) 4685
53. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 37 (1998) 3387
54. Zapf A., Ehrentraut A., and Beller M. Angew. Chem., Int. Ed. 39 (2000) 4153
55. Zhang C., Huang J., Trudell M.L., and Nolan S.P. J. Org. Chem. 64 (1999) 3804
56. Navarro O., Kelly R.A., and Nolan S.P. J. Am. Chem. Soc. 125 (2003) 16194
57. Ackermann L., and Born R. Angew. Chem., Int. Ed. 44 (2005) 2444
58. Colacot T.J., and Shea H.A. Org. Lett. 6 (2004) 3731
59. Botella L., and Nájera C. Angew. Chem., Int. Ed. 41 (2002) 179
60. Dai Q., Gao W., Liu D., Kapes L.M., and Zhang X. J. Org. Chem. 71 (2006) 3928
61. Würtz S., and Glorius F. Acc. Chem. Res. 41 (2008) 1523
62. Inada K., and Miyaura N. Tetrahedron 56 (2000) 8661
63. Parrish C.A., and Buchwald S.L. J. Org. Chem. 66 (2001) 3820
64. Glegola K., Framery E., Pietrusiewicz K.M., and Sinou D. Adv. Synth. Catal. 348 (2006) 1728
65. Bedford R.B., Coles S.J., Hursthouse M.B., and Scordia V.J.M. Dalton Trans. (2005) 991
66. Sommer W.J., and Weck M. Adv. Synth. Catal. 348 (2006) 2101
67. Leyva A., García H., and Corma A. Tetrahedron 63 (2007) 7097
68. Colacot T.J., Carole W.A., Neide B.A., and Harad A. Organometallics 27 (2008) 5605
69. Schweizer, S.; Becht, J.-M.; Le Drian, C. Fr. Patent FR2,914,867, Application Nr. 2007-54500, April/16/2007; PCT Extension FR2008/050639, April/11/2008 (University of Haute Alsace/CNRS).
70. 2O or THF), replacing the alkyllithium reagents with the corresponding Grignard reagents, but all were unsuccessful.
71. Attempts to store the chlorophosphines several days under an atmosphere of argon at low temperature were unsuccessful.
72. Fieser L.F., Berliner E., Bondhus F.J., Chang F.C., Dauben W.G., Ettlinger M.G., Fawaz G., Fields M., Heidelberger C., Heymann H., Vaughan W.R., Wilson A.G., Wilson E., Wu M.-i., Leffler M.T., Hamlin K.E., Moore E.E., Moore M.B., and Zaugg H.E. J. Am. Chem. Soc. 70 (1948) 3177
73. Wallow T.I., and Novak B.M. J. Org. Chem. 59 (1994) 5034
74. Berlman I.B., Wirth H.O., and Steingraber O.J. J. Am. Chem. Soc. 90 (1968) 566
75. Gomberg M., and Pernet J.C. J. Am. Chem. Soc. 48 (1926) 1372
76. Shi M., and Qian H.-x. Tetrahedron 21 (2005) 4949
77. Eliel E.L., and Daignault R.A. J. Org. Chem. 30 (1965) 2450
78. Terao Y., Wakui H., Nomoto N., Satoh T., Miura M., and Nomura M. J. Org. Chem. 68 (2003) 5236
79. Zhu L., Duquette J., and Zhang M. J. Org. Chem. 68 (2003) 3729
80. Berliner E., and Liu L.H. J. Org. Chem. 75 (1953) 2417
81. Dawood K.M., and Kirschning A. Tetrahedron 61 (2005) 12121
82. Mowery M.E., and De-Shong P. J. Org. Chem. 64 (1999) 3266
83. Bradsher C.K., Brown F.C., and Porter H.K. J. Am. Chem. Soc. 76 (1954) 2357
84. Kasahara I., Tachi I., Tsuda E., Hata N., Taguchi S., and Goto K. Analyst 114 (1989) 1479