Palladacycles in catalysis - A critical survey

Journal of Organometallic Chemistry

Volumn 689, Issue 24 SPEC. ISS., 2004, Pages 4055-4082

  Beletskaya, Irina P ^a   Cheprakov, Andrei V ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Catalysis; Cross coupling; Heck reaction; Palladacycle; Palladium; Pincer

Indexed keywords

ORGANOMETALLICS; PALLADIUM;

CROSS-COUPLING; PALLADACYCLES;

CATALYSIS;

IMINE; OXIME DERIVATIVE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE;

CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; REVIEW;

EID: 9944245910     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2004.07.054     Document Type: Review

References (142)

1. W.A. Herrmann, C. Brossmer, K. Ofele, C.P. Reisinger, T. Priermeier, M. Beller, and H. Fischer Angew. Chem., Int. Ed. Engl. 34 1995 1844
2. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009
3. M. Catellani Synlett 2003 298
4. A.M. Echavarren, B. Gomez-Lor, J.J. Gonzalez, and O. de Frutos Synlett 2003 585
5. G. Dyker Chem. Ber./Recueil 130 1997 1567
6. T. Satoh, J.-I. Inoh, Y. Kawamura, M. Miura, and M. Nomura Bull. Chem. Soc. Jpn. 71 1998 2239
7. T. Satoh, T. Itaya, M. Miura, and M. Nomura Chem. Lett. 9 1996 823
8. T. Satoh, Y. Kawamura, M. Miura, and M. Nomura Angew. Chem., Int. Ed. Engl. 36 1997 1740
9. T. Harayama, T. Sato, A. Hori, H. Abe, and Y. Takeuchi Synlett 2003 1141
10. Y. Terao, Y. Fukuoka, T. Satoh, M. Miura, and M. Nomura Tetrahedron Lett. 43 2002 101
11. A. Carbayo, J.V. Cuevas, and G. Garcia-Herbosa J. Organomet. Chem. 658 2002 15
12. S.G. Fiddy, J. Evans, M.A. Newton, T. Neisius, R.P. Tooze, and R. Oldman Chem. Commun. 2003 2682
13. W.A. Herrmann, K. Ofele, D. Von Preysing, and S.K. Schneider J. Organomet. Chem. 687 2003 229
14. J. Dupont, M. Pfeffer, and J. Spencer Eur. J. Inorg. Chem. 2001 1917
15. R.B. Bedford Chem. Commun. 2003 1787
16. I.P. Beletskaya, A.N. Kashin, N.B. Karlstedt, A.V. Mitin, A.V. Cheprakov, and G.M. Kazankov J. Organomet. Chem. 622 2001 89
17. M.T. Reetz, and E. Westermann Angew. Chem. Int. Ed. 39 2000 165
18. A. Biffis, M. Zecca, and M. Basato Eur. J. Inorg. Chem. 2001 1131
19. C. Amatore, and A. Jutand J. Organomet. Chem. 576 1999 254
20. M.T. Reetz, E. Westermann, R. Lohmer, and G. Lohmer Tetrahedron Lett. 39 1998 8449
21. I.P. Beletskaya, and A.V. Cheprakov S.-I. Murahashi S.G. Davies Transition Metal Catalyzed Reactions 1999 Blackwell Science Oxford 29
22. A.H.M. de Vries, J. Mulders, J.H.M. Mommers, H.J.W. Henderickx, and J.G. de Vries Org. Lett. 5 2003 3285
23. A.H.M. de Vries, F.J. Parlevliet, L. Schmieder-van deVondervoort, J.H.M. Mommers, H.J.W. Henderickx, M.A.M. Walet, and J.G. de Vries Adv. Synth. Catal. 344 2002 996
24. A.S. Gruber, D. Pozebon, A.L. Monteiro, and J. Dupont Tetrahedron Lett. 42 2001 7345
25. Q.W. Yao, E.P. Kinney, and Z. Yang J. Org. Chem. 68 2003 7528
26. S. Iyer, G.M. Kulkarni, and C. Ramesh Tetrahedron 60 2004 2163
27. T. Jeffery J. Chem. Soc., Chem. Commun. 19 1984 1287
28. T. Jeffery Tetrahedron Lett. 35 1994 3051
29. T. Jeffery L.S. Liebeskind Advances in Metal-Organic Chemistry vol. 5 1996 Jai Press Greenwich, CT
30. T. Jeffery, and M. David Tetrahedron Lett. 39 1998 5751
31. T. Jeffery Tetrahedron 52 1996 10113
32. S.S. Prockl, W. Kleist, M.A. Gruber, and K. Kohler Angew. Chem. Int. Ed. 43 2004 1881
33. V.V. Bykov, N.A. Bumagin, and I.P. Beletskaya Dokl. Akad. Nauk. SSSR 340 1995 775
34. I.P. Beletskaya, and A.V. Cheprakov E.-I. Negishi Handbook of Organopalladium Chemistry vol. 2 2002 Wiley New York 2957
35. M. Beller, H. Fischer, W.A. Herrmann, K. Ofele, and C. Brossmer Angew. Chem., Int. Ed. Engl. 34 1995 1848
36. W.A. Herrmann, and V.P.W. Bohm J. Organomet. Chem. 572 1999 141
37. V.P.W. Bohm, and W.A. Herrmann Chem. Eur. J. 7 2001 4191
38. M. Beller, and T.H. Riermeier Tetrahedron Lett. 37 1996 6535
39. M. Beller, and T.H. Riermeier Eur. J. Inorg. Chem. 1998 29
40. L.J. Xu, J. Mo, C. Baillie, and J.L. Xiao J. Organomet. Chem. 687 2003 301
41. L.F. Tietze, H. Schirok, M. Wohrmann, and K. Schrader Eur. J. Org. Chem. 2000 2433
42. L.F. Tietze, and A. Modi Med. Res. Rev. 20 2000 304
43. L.F. Tietze, K.M. Sommer, G. Schneider, P. Tapolcsanyi, J. Wolfling, P. Muller, M. Noltemeyer, and H. Terlau Synlett 2003 1494
44. W.A. Herrmann, C. Brossmer, C.P. Reisinger, T.H. Riermeier, K. Ofele, and M. Beller Chem. Eur. J. 3 1997 1357
45. C.A. Lin, and F.T. Luo Tetrahedron Lett. 44 2003 7565
46. S. Gibson, D.F. Foster, G.R. Eastham, R.P. Tooze, and D.J. Cole-Hamilton Chem. Commun. 2001 779
47. M.M. Pereira, G. Muller, J.I. Ordinas, M.E. Azenha, and L.G. Arnaut J. Chem. Soc., Perkin Trans. 2 2002 1583
48. B.L. Shaw, S.D. Perera, and E.A. Staley Chem. Commun. 1998 1361
49. J.M. Brunel, A. Heumann, and G. Buono Angew. Chem. Int. Ed. 39 2000 1946
50. J.M. Brunel, M.H. Hirlemann, A. Heumann, and G. Buono Chem. Commun. 2000 1869
51. M. Catellani, and G.P. Chiusoli J. Organomet. Chem. 437 1992 369
52. M. Catellani, and G.P. Chiusoli J. Organomet. Chem. 425 1992 151
53. M. Catellani, B. Marmiroli, M.C. Fagnola, and D. Acquotti J. Organomet. Chem. 507 1996 157
54. M. Catellani, F. Frignani, and A. Rangoni Angew. Chem., Int. Ed. Engl. 36 1997 119
55. M. Catellani, F. Cugini, and G. Bocelli J. Organomet. Chem. 584 1999 63
56. M. Catellani, E. Motti, and L. Paterlini J. Organomet. Chem. 594 2000 240
57. M. Catellani, S. Deledda, B. Ganchegui, F. Henin, E. Motti, and J. Muzart J. Organomet. Chem. 687 2003 473
58. M. Catellani, E. Motti, and M. Minari Chem. Commun. 2000 157
59. F.F. Paintner, K. Gorler, and W. Voelter Synlett 2003 522
60. M.S. Brody, and M.G. Finn Tetrahedron Lett. 40 1999 415
61. D.D. Hennings, T. Iwama, and V.H. Rawal Org. Lett. 1 1999 1205
62. M. Beller, and A. Zapf Synlett 7 1998 792
63. D.A. Albisson, R.B. Bedford, and P.N. Scully Tetrahedron Lett. 39 1998 9793
64. D.A. Albisson, R.B. Bedford, S.E. Lawrence, and P.N. Scully Chem. Commun. 1998 2095
65. R.B. Bedford, S.L. Hazlewood, M.E. Limmert, D.A. Albisson, S.M. Draper, P.N. Scully, S.J. Coles, and M.B. Hursthouse Chem. Eur. J. 9 2003 3216
66. J.P. Wolfe, R.A. Singer, B.H. Yang, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 9550
67. R.B. Bedford, and S.L. Welch Chem. Commun. 2001 129
68. G.R. Rosa, G. Ebeling, J. Dupont, and A.L. Monteiro Synthesis 2003 2894
69. L.N. Lewis J. Am. Chem. Soc. 108 1986 743
70. M. Ohff, A. Ohff, and D. Milstein Chem. Commun. 1999 357
71. D.G. Blackmond, T. Rosner, and A. Pfaltz Org. Proc. Res. Dev. 3 1999 275
72. C. Rocaboy, and J.A. Gladysz New J. Chem. 27 2003 39
73. T. Rosner, A. Pfaltz, and D.G. Blackmond J. Am. Chem. Soc. 123 2001 4621
74. T. Rosner, J. Le Bars, A. Pfaltz, and D.G. Blackmond J. Am. Chem. Soc. 123 2001 1848
75. M. Nowotny, U. Hanefeld, H. van Koningsveld, and T. Maschmeyer Chem. Commun. 2000 1877
76. Y.J. Wu, J.J. Hou, H.Y. Yun, X.L. Cui, and R.J. Yuan J. Organomet. Chem. 637 2001 793
77. C. Rocaboy, and J.A. Gladysz Org. Lett. 4 2002 1993
78. H. Weissman, and D. Milstein Chem. Commun. 1999 1901
79. S. Iyer, and C. Ramesh Tetrahedron Lett. 41 2000 8981
80. D.A. Alonso, C. Najera, and M.C. Pacheco Org. Lett. 2 2000 1823
81. S. Iyer, and A. Jayanthi Tetrahedron Lett. 42 2001 7877
82. D.A. Alonso, C. Najera, and M.C. Pacheco Adv. Synth. Catal. 344 2002 172
83. D.A. Alonso, C. Najera, and M.C. Pacheco J. Org. Chem. 67 2002 5588
84. L. Botella, and C. Najera Angew. Chem. Int. Ed. 41 2002 179
85. L. Botella, and C. Najera J. Organomet. Chem. 663 2002 46
86. C. Baleizao, A. Corma, H. Garcia, and A. Leyva Chem. Commun. 2003 606
87. C. Baleizao, A. Corma, H. Garcia, and A. Leyva J. Org. Chem. 69 2004 439
88. C. Ramesh, Y. Kubota, M. Miwa, and Y. Sugi Synthesis-Stuttgart 2002 2171
89. F. Yang, Y.M. Zhang, R. Zheng, J. Tang, and M.Y. He J. Organomet. Chem. 651 2002 146
90. K. Isobe, and S. Kawaguchi Heterocycles 16 1981 1603
91. A. Beeby, S. Bettington, I.J.S. Fairlamb, A.E. Goeta, A.R. Kapdi, E.H. Niemela, and A.L. Thompson New J. Chem. 28 2004 600
92. C.S. Consorti, M.L. Zanini, S. Leal, G. Ebeling, and J. Dupont Org. Lett. 5 2003 983
93. T. Mino, Y. Shirae, M. Sakamoto, and T. Fujita Synlett 2003 882
94. V.V. Thakur, N.S.C.R. Kumar, and A. Sudalai Tetrahedron Lett. 45 2004 2915 2918
95. A.S. Gruber, D. Zim, G. Ebeling, A.L. Monteiro, and J. Dupont Org. Lett. 2 2000 1287
96. D. Zim, A.S. Gruber, G. Ebeling, J. Dupont, and A.L. Monteiro Org. Lett. 2 2000 2881
97. D. Zim, A.L. Monteiro, and J. Dupont Tetrahedron Lett. 41 2000 8199
98. J. Dupont, A.S. Gruber, G.S. Fonseca, A.L. Monteiro, G. Ebeling, and R.A. Burrow Organometallics 20 2001 171
99. M. Albrecht, and G. van Koten Angew. Chem. Int. Ed. 40 2001 3750
100. J.T. Singleton Tetrahedron 59 2003 1837
101. M.E. van der Boom, and D. Milstein Chem. Rev. 103 2003 1759
102. M. Ohff, A. Ohff, M.E.V.D. Boom, and D. Milstein J. Am. Chem. Soc. 119 1997 11687
103. K. Kiewel, Y.S. Liu, D.E. Bergbreiter, and G.A. Sulikowski Tetrahedron Lett. 40 1999 8945
104. I.P. Beletskaya, A.V. Chuchurjukin, H.P. Dijkstra, G.P.M. van Klink, and G. van Koten Tetrahedron Lett. 41 2000 1075
105. R. Chanthateyanonth, and H. Alper J. Mol. Cat. (A) 201 2003 23
106. S. Sjovall, O.F. Wendt, and C. Andersson J. Chem. Soc., Dalton Trans. 2002 1396
107. F. Miyazaki, K. Yamaguchi, and M. Shibasaki Tetrahedron Lett. 40 1999 7379
108. D. Morales-Morales, C. Grause, K. Kasaoka, R. Redon, R.E. Cramer, and C.M. Jensen Inorg. Chim. Acta 300 2000 958
109. D. Morales-Morales, R. Redon, C. Yung, and C.M. Jensen Chem. Commun. 2000 1619
110. M.R. Eberhard, Z.H. Wang, and C.M. Jensen Chem. Commun. 2002 818
111. R.B. Bedford, S.M. Draper, P.N. Scully, and S.L. Welch New J. Chem. 24 2000 745
112. Z.H. Wang, M.R. Eberhard, C.M. Jensen, S. Matsukawa, and Y. Yamamoto J. Organomet. Chem. 681 2003 189
113. A.J. Blacker, M.L. Clarke, M.S. Loft, M.F. Mahon, M.E. Humphries, and J.M.J. Williams Chem. Eur. J. 6 2000 353
114. I.G. Jung, S.U. Son, K.H. Park, K.C. Chung, J.W. Lee, and Y.K. Chung Organometallics 22 2003 4715
115. E. Diez-Barra, J. Guerra, V. Hornillos, S. Merino, and J. Tejeda Organometallics 22 2003 4610
116. D.E. Bergbreiter, P.L. Osburn, and Y.S. Liu J. Am. Chem. Soc. 121 1999 9531
117. D.E. Bergbreiter, P.L. Osburn, A. Wilson, and E.M. Sink J. Am. Chem. Soc. 122 2000 9058
118. D.E. Bergbreiter, and J. Li Chem. Commun. 2004 42
119. A. Schnyder, A.F. Indolese, M. Studer, and H.U. Blaser Angew. Chem. Int. Ed. 41 2002 3668
120. R.B. Bedford, S.L. Hazelwood, M.E. Limmert, J.M. Brown, S. Ramdeehul, A.R. Cowley, S.J. Coles, and M.B. Hursthouse Organometallics 22 2003 1364
121. R.B. Bedford, C.S.J. Cazin, S.J. Coles, T. Gelbrich, M.B. Hursthouse, and V.J.M. Scordia J. Chem. Soc., Dalton Trans. 2003 3350
122. R.B. Bedford, and C.S.J. Cazin Chem. Commun. 2001 1540
123. C.W.K. Gstottmayr, V.P.W. Bohm, E. Herdtweck, M. Grosche, and W.A. Herrmann Angew. Chem. Int. Ed. 41 2002 1363
124. O. Navarro, R.A. Kelly, and S.P. Nolan J. Am. Chem. Soc. 125 2003 16194
125. G. Altenhoff, R. Goddard, C.W. Lehmann, and F. Glorius Angew. Chem. Int. Ed. 42 2003 3690
126. S. Iyer, and A. Jayanthi Synlett 2003 1125
127. M.S. Viciu, R.A. Kelly, E.D. Stevens, F. Naud, M. Studer, and S.P. Nolan Org. Lett. 5 2003 1479
128. M.S. Viciu, R.M. Kissling, E.D. Stevens, and S.P. Nolan Org. Lett. 4 2002 2229
129. N. Marion, O. Navarro, R.A. Kelly, and S.P. Nolan Synthesis 2003 2590
130. M.S. Viciu, R.F. Germaneau, and S.P. Nolan Org. Lett. 4 2002 4053
131. H. Palencia, F. Garcia-Jimenez, and J.M. Takacs Tetrahedron Lett. 45 2004 3849
132. Y. Donde, and L.E. Overman J. Am. Chem. Soc. 121 1999 2933
133. J. Kang, K.H. Yew, T.H. Kim, and D.H. Choi Tetrahedron Lett. 43 2002 9509
134. C.E. Anderson, and L.E. Overman J. Am. Chem. Soc. 125 2003 12412
135. L.E. Overman, C.E. Owen, M.M. Pavan, and C.J. Richards Org. Lett. 5 2003 1809
136. H.P. Dijkstra, M.Q. Slagt, A. McDonald, C.A. Kruithof, R. Kreiter, A.M. Mills, M. Lutz, A.L. Spek, W. Klopper, G.P.M. van Klink, and G. van Koten Eur. J. Inorg. Chem. 2003 830
137. K. Takenaka, and Y. Uozumi Org. Lett. 6 2004 1833
138. H.P. Dijkstra, N. Ronde, G.P.M. van Klink, D. Vogt, and G. van Koten Adv. Synth. Catal. 345 2003 364
139. H.P. Dijkstra, M.D. Meijer, J. Patel, R. Kreiter, G.P.M. van Klink, M. Lutz, A.L. Spek, A.J. Canty, and G. van Koten Organometallics 20 2001 3159
140. W.D. Cotter, L. Barbour, K.L. McNamara, R. Hechter, and R.J. Lachicotte J. Am. Chem. Soc. 120 1998 11016
141. N. Solin, J. Kjellgren, and K.J. Szabo Angew. Chem. Int. Ed. 42 2003 3656
142. J. Kjellgren, H. Sunden, and K.J. Szabo J. Am. Chem. Soc. 126 2004 474