Palladium-catalysed reactions of alcohols. Part B: Formation of C-C and C-N bonds from unsaturated alcohols

Tetrahedron

Volumn 61, Issue 17, 2005, Pages 4179-4212

  Muzart, Jacques ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Alcohols; Amination; Arylation; Palladium; Umpolung; Vinylation; 3 Allylpalladium

Indexed keywords

ALCOHOL; ALCOHOL DERIVATIVE; CARBON; PALLADIUM;

ADDITION REACTION; AMINOPALLADATION; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; MOLECULAR INTERACTION; PRIORITY JOURNAL; REVIEW; VINYLATION;

EID: 16244407390     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.02.026     Document Type: Review

References (318)

1. Part A: 'Palladium-Catalyzed Oxidation of Primary and Secondary Alcohols' J. Muzart Tetrahedron 31 2003 5789 5816
2. J. Muzart, J.-P. Genêt, and A. Denis J. Organomet. Chem. 326 1987 C23 C28
3. A. Arcadi, E. Bernocchi, A. Burini, S. Cacchi, F. Marinelli, and B. Pietroni Tetrahedron 44 1988 481 490
4. J. Nokami, H. Ogawa, S. Miyamoto, T. Mandai, S. Wakabayashi, and J. Tsuji Tetrahedron Lett. 29 1988 5181 5184
5. E. Negishi, S. Iyer, and C.J. Rousset Tetrahedron Lett. 40 1989 291 294
6. K. Zaw, and P.M. Henry J. Org. Chem. 55 1990 1842 1847
7. A. Arcadi, S. Cacchi, and F. Marinelli Tetrahedron 49 1993 4955 4964
8. H. Pellissier, S. Wilmouth, and M. Santelli Tetrahedron Lett. 37 1996 5107 5110
9. G.V.M. Sharma, A.S. Chander, K. Krishnudu, and P.R. Krishna Tetrahedron Lett. 38 1997 9051 9054
10. A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, and P. Pace Eur. J. Org. Chem. 1999 3305 3313
11. S. Ma, and S. Zhao J. Am. Chem. Soc. 123 2001 5578 5579
12. W. Zhu, and D. Ma Org. Lett. 51 2003 5063 5066
13. H. Yuasa, G. Makado, and Y. Fukuyama Tetrahedron Lett. 44 2003 6235 6239
14. B. Salem, P. Klotz, and J. Suffert Synthesis 2004 298 307
15. H. Hattori, A.A. Abbas, and Y. Kobayashi Chem. Commun. 2004 884 885
16. H. Nagano, M. Yokota, and Y. Iwazaki Tetrahedron Lett. 45 2004 3035 3037
17. R. Schiller, M. Pour, H. Fáková, J. Kuneš, and I. Císaŕová J. Org. Chem. 69 2004 6761 6765
18. M. Oestreich, F. Sempere-Culler, and A.B. Machotta Angew. Chem. Int. Ed. 44 2005 149 152
19. R.F. Heck J. Am. Chem. Soc. 90 1968 5526 5531
20. J.B. Melpolder, and R.F. Heck J. Org. Chem. 41 1976 265 272
21. A.J. Chalk, and S.A. Magennis J. Org. Chem. 41 1976 273 278
22. IV intermediates and discussion, see: (a) 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 1848
23. M. Beller, H. Fischer, W.A. Herrmann, K. Ofele, and C. Brossmer Angew. Chem., Ind. Ed. Engl. 34 1995 1848 1849
24. M. Beller, and T.H. Riermeier Tetrahedron Lett. 37 1996 6535 6538
25. B.L. Shaw New J. Chem. 22 1998 77 79
26. B.L. Shaw, S.D. Perera, and E.A. Staley Chem. Commun. 1998 1361 1362
27. W.A. Herrmann, V.P.W. Böhm, and C.-P. Reisinger J. Organomet. Chem. 576 1999 23 41
28. F. Miyazaki, K. Yamaguchi, and M. Shibasaki Tetrahedron Lett. 40 1999 7379 7383
29. A.S. Gruber, D. Zim, G. Ebeling, A.L. Monteiro, and J. Dupont Org. Lett. 2 2000 1287 1290
30. A. Sundermann, O. Uzan, and J.M.L. Martin Chem. Eur. J. 7 2001 1703 1711
31. K. Yu, W. Sommer, M. Weck, and C.W. Jones J. Catal. 226 2004 101 110
32. For a more elaborated mechanism of the Heck reaction, see: (a) C. Amatore, A. Jutand, and M.A. M'Barki Organometallics 11 1992 3009 3013
33. C. Amatore, M. Carré, A. Jutand, and M.A. M'Barki Organometallics 14 1995 1818 1826
34. C. Amatore, M. Carré, A. Jutand, M.A. M'Barki, and G. Meyer Organometallics 14 1995 5605 5614
35. (d) Amatore, C.; Jutand, A. Sciences Chimiques, Lettres des Départements Scientifiques du CNRS 1996/97, 59 22-26.
36. For the mechanism of the oxidative addition of aryl halides to Pd catalysts, see: L.J. Gooßen, D. Koley, H. Hermann, and W. Thiel Chem. Commun. 2004 2141 2143
37. For the detection of the HPdX intermediate, see: I.D. Hills, and G.C. Fu J. Am. Chem. Soc. 126 2004 13178 13179
38. Y. Tamaru, Y. Yamada, and Z. Yoshida Tetrahedron 35 1979 329 340
39. M. Aslam, V. Elango, and K.G. Davenport Synthesis 1989 869 870
40. Beecham Group PLC, UK, Neth. Appl. NL 8803088, 1989; Chem. Abstr. 112, 20797.
41. M. Beller, and A. Zapf Synlett 1998 792 793
42. S. Bouquillon, B. Ganchegui, B. Estrine, F. Hénin, and J. Muzart J. Organomet. Chem. 634 2001 153 156
43. V. Caló, A. Nacci, A. Monopoli, and M. Spinelli Eur. J. Org. Chem. 2003 1382 1385
44. V. Caló, A. Nacci, and A. Monopoli J. Mol. Catal. A: Chem. 214 2004 45 56
45. T. Jeffery J. Chem. Soc., Chem. Commun. 1984 1287 1289
46. C. Käpplinger, and R. Beckert Synthesis 2002 1843 1850
47. N. Sundar, and S.V. Bhat Synth. Commun. 28 1998 2311 2316
48. J.-L. Reymond, C.K. Jahangiri, C. Stoudt, and R.A. Lerner J. Am. Chem. Soc. 115 1993 3909 3917
49. J.-L. Reymond, and Y. Chen J. Org. Chem. 60 1995 6970 6979
50. R. Kumareswaran, and Y.D. Vankar Synth. Commun. 28 1998 2291 2302
51. M.Z. Cai, C.S. Song, and X. Huang Chin. Chem. Lett. 9 1998 427 430
52. S.B. Solabannavar, P.P. Wadgaonkar, U.V. Desai, and R.B. Mane Org. Prep. Proc. Int. 35 2003 418 420
53. S.B. Solabannavar, V.B. Helavi, U.V. Desai, and R.B. Mane Synth. Commun. 33 2003 361 365
54. R.C. Larock, W.-Y. Leung, and S. Stolz-Dunn Tetrahedron Lett. 30 1989 6629 6632
55. T. Jeffery Tetrahedron Lett. 32 1991 2121 2124
56. E.C. Taylor, P. Gillepsie, and M. Patel J. Org. Chem. 57 1992 3218 3225
57. S.E. Watson, E.C. Taylor, and M. Patel Synth. Commun. 28 1998 1897 1905
58. E.C. Taylor, and B. Liu Tetrahedron Lett. 40 1999 4023 4026
59. C.J. Barnett, and T.M. Wilson Heterocycles 35 1993 925 936
60. R.C. Larock, E.K. Yum, and H. Yang Tetrahedron 50 1994 305 321
61. S. Sengupta, and S.K. Sadhukhan Tetrahedron Lett. 39 1998 1237 1238
62. D. Basavaiah, and K. Muthukumaran Tetrahedron 54 1998 4943 4948
63. J.-R. Labrosse, C. Poncet, P. Lhoste, and D. Sinou Tetrahedron: Asymmetry 10 1999 1069 1078
64. D. Villemin, and B. Nechab J. Chem. Res. (S) 2000 429 431
65. L.F. Tietze, J. Görlitzer, A. Schuffenhauer, and M. Hübner Eur. J. Org. Chem. 1999 1075 1084
66. D. Bruyère, G. Gaignard, D. Bouyssi, G. Balme, and J.-M. Lancelin Tetrahedron Lett. 38 1997 827 830
67. G. Pattenden, and P. Wiedenau Tetrahedron Lett. 38 1997 3647 3650
68. A. Patwa, A. Zanka, M.P. Cassidy, and J.M. Harris Tetrahedron 59 2003 4939 4944
69. S.E. Gibson (née Thomas), J.O. Jones, R. McCague, M.J. Tozer, and N.J. Whitcombe Synlett 1999 954 956
70. L.F. Tietze, K. Kahle, and T. Raschke Chem. Eur. J. 8 2002 401 407
71. H. Zhao, M.-Z. Cai, R.-H. Hu, and C.-S. Song Synth. Commun. 31 2001 3665 3669
72. V. Caló, A. Nacci, L. Lopez, and A. Napola Tetrahedron Lett. 42 2001 4701 4703
73. V. Caló, and A. Nacci Z. Naturforsch. 56a 2001 702 706
74. F. Berthiol, H. Doucet, and M. Santelli Tetrahedron Lett. 45 2004 5633 5636
75. W. Smadja, S. Czernecki, G. Ville, and C. Georgoulis Tetrahedron Lett. 22 1981 2479 2482
76. W. Smadja, G. Ville, and G. Cahiez Tetrahedron Lett. 25 1984 1793 1796
77. R. Benhaddou, S. Czernecki, and G. Ville J. Chem. Soc., Chem. Commun. 1988 247 248
78. R. Benhaddou, S. Czernecki, G. Ville, and A. Zegar Organometallics 7 1988 2435 2439
79. W. Smadja, S. Czernecki, G. Ville, and C. Georgoulis Organometallics 6 1987 166 169
80. L. Bagnell, U. Kreher, and C.R. Strauss Chem. Commun. 2001 29 30
81. J. Li, A.W.-H. Mau, and C.R. Strauss Chem. Commun. 1997 1275 1278
82. T. Satoh, M. Miura, and M. Nomura J. Mol. Catal. A: Chem. 112 1996 211 215
83. Y. Tamaru, Y. Yamamoto, Y. Yamada, and Z. Yoshida Tetrahedron Lett. 1979 1401 1404
84. Y. Tamaru, K. Inoue, Y. Yamada, and Z. Yoshida Tetrahedron Lett. 22 1981 1801 1802
85. Y. Tamaru, Y. Yamada, K. Inoue, Y. Yamamoto, and Z. Yoshida J. Org. Chem. 48 1983 1286 1292
86. B.M. Choudary, and M.L. Lakshmi Kantam J. Mol. Catal. 36 1986 343 347
87. B.M. Choudary, N.P. Prabhakar Reddy, M.L. Lakshmi Kantam, and Z. Jamil Tetrahedron Lett. 26 1985 6257 6258
88. B.M. Choudary, S.S. Shobha Rani, Y.V. Subba Rao, and M.L. Lakshmi Kantam J. Chem. Soc., Perkin Trans. 1 1991 2274 2275
89. A. Bessmertnykh, F. Hénin, and J. Muzart Carbohydr. Res. 339 2004 1377 1380
90. A.F. Littke, and G.C. Fu J. Am. Chem. Soc. 123 2001 6989 7000
91. B.A. Patel, and R.F. Heck J. Org. Chem. 43 1978 3898 3903
92. L.-C. Kao, F.G. Stakem, B.A. Patel, and R.F. Heck J. Org. Chem. 47 1982 1267 1277
93. S. Torii, H. Okumoto, F. Akahoshi, and T. Kotani J. Am. Chem. Soc. 111 1989 8932 8934
94. R.C. Larock, F. Kondo, K. Narayanan, L.K. Sydnes, and M.-F.H. Hsu Tetrahedron Lett. 30 1989 5737 5740
95. S. Torii, H. Okumoto, and T. Kotani Synlett 1992 349 350
96. A. Briot, C. Baehr, R. Brouillard, A. Wagner, and C. Mioskowski J. Org. Chem. 69 2004 1374 1377
97. K. Yonehara, K. Mori, T. Hashizume, K.-G. Chung, K. Ohe, and S. Uemura J. Organomet. Chem. 603 2000 40 49
98. S. Bouquillon, S. Humbel, U. Létinois-Halbes, F. Hénin, and J. Muzart J. Organomet. Chem. 687 2003 377 383
99. Ganchegui, B. Ph.D. Thesis Reims, 2004.
100. G. Dyker, and A. Thöne J. Prakt. Chem. 341 1993 138 141
101. G. Dyker, D. Kadzimirsz, and G. Henkel Tetrahedron Lett. 44 2003 7905 7907
102. M. Catellani, S. Deledda, B. Ganchegui, F. Hénin, E. Motti, and J. Muzart J. Organomet. Chem. 687 2003 473 482
103. M. Catellani, and E. Motti New J. Chem. 22 1998 759 761
104. M. Catellani, E. Motti, and S. Baratta Org. Lett. 3 2001 3611 3614
105. H. Nagashima, K. Sato, and J. Tsuji J. Chem. Lett. 1981 1605 1608
106. H. Nagashima, K. Sato, and J. Tsuji Tetrahedron 41 1985 5645 5651
107. J. Tsuji, H. Nagashima, and K. Sato Tetrahedron Lett. 23 1982 3085 3088
108. S.-K. Kang, H.-W. Lee, S.-B. Jang, T.-H. Kim, and S.-J. Pyun J. Org. Chem. 41 1976 2604 2605
109. A. Nishimura, M. Uchiyama, T. Suzuki, and Y. Yamazaki Nippon Kagaku Kaishi 1985 558 560 Chem. Abstr. 1986, 104, 109137
110. K. Kikuwa, and T. Matsuda Chem. Lett. 1977 159 162
111. K. Kikuwa, K. Nagira, F. Wada, and T. Matsuda Tetrahedron 37 1981 31 36
112. R.-H. Hu, X.-L. Liu, and M.-Z. Cai Jiangxi Shifan Daxue Xuebao Ziran Kexueban 25 2001 246 250 Chem. Abstr. 136, 355024
113. T. Jeffery Tetrahedron Lett. 31 1990 6641 6644
114. T. Jeffery J. Chem. Soc., Chem. Commun. 1991 324 325
115. 62 it appears that the nature of the counterion of the diaryiodonium salt and the experimental conditions have a determining effect on the regioselectivity of the β-H elimination.
116. B.M. Trost, and D.C. Lee J. Org. Chem. 54 1989 2271 2274
117. G.A. Grasa, R. Singh, E.D. Stevens, and S.P. Nolan J. Organomet. Chem. 687 2003 269 279
118. T. Mandai, S. Hasegawa, T. Fujimoto, M. Kawada, J. Nokami, and J. Tsuji Synlett 1990 85 86
119. S.-K. Kang, K.-Y. Jung, C.-H. Park, E.-Y. Namkoong, and T.-H. Kim Tetrahedron Lett. 36 1996 6287 6290
120. N. Cheeseman, M. Fox, M. Jackson, I.C. Lennon, and G. Meek Proc. Natl. Acad. Sci. U.S.A. 101 2004 5396 5399
121. J. Nokami, A. Furukawa, Y. Okuda, A. Hazato, and S. Kurozumi Tetrahedron Lett. 39 1998 1005 1008
122. G. Dyker, P. Grundt, H. Markwitz, and G. Henkel J. Org. Chem. 63 1998 6043 6047
123. G. Dyker, H. Markwitz, and G. Henkel Eur. J. Org. Chem. 2001 2415 2423
124. S.E. Gibson, J.O. Jones, S.B. Kalindjian, J.D. Knight, N. Mainolfi, M. Rudd, J.W. Steed, M.J. Tozer, and P. Wright Tetrahedron 60 2004 6945 6958
125. Y. Wong, X. Dong, and R.C. Larock J. Org. Chem. 68 2003 3090 3098
126. J. Tsuji, T. Yamakawa, M. Kaito, and T. Mandai Tetrahedron Lett. 1978 2075 2078
127. I. Shimizu, T. Sugiura, and J. Tsuji J. Org. Chem. 50 1985 537 539
128. E. Keinan, S. Kumar, V. Dangur, and J. Vaya J. Am. Chem. Soc. 116 1994 11151 11152
129. P.G. Andersson, and S. Schab Organometallics 14 1995 1 2
130. S. Cacchi, M. Felici, and B. Pietroni Tetrahedron Lett. 25 1984 3137 3140
131. A. Arcadi, S. Cacchi, and F. Marinelli Tetrahedron 41 1985 5121 5131
132. S. Cacchi, G. Fabrizi, and A. Goggiamani J. Mol. Catal. A: Chem. 214 2004 57 64
133. T.J.J. Müller, M. Ansorge, and D. Aktah Angew. Chem. Int. Ed. 39 2000 1253 1256
134. N.G. Kundu, and P. Das J. Chem. Soc., Chem. Commun. 1995 99 100
135. P. Das, and N.G. Kundu J. Chem. Res. (S) 1996 298 299
136. N.G. Kundu, P. Das, J. Balzarini, and E. De Clercq Bioorg. Med. Chem. 5 1997 2011 2018
137. A. Coelho, E. Sotelo, and E. Raviña Tetrahedron 59 2003 2477 2484
138. A. Coelho, E. Sotelo, H. Novoa, O.M. Peeters, N. Blaton, and E. Raviña Tetrahedron 60 2004 12177 12189
139. K. Minn Synlett 1991 115 116
140. A. Ohsawa, Y. Abe, and H. Igeta Chem. Lett. 1979 241 244
141. A. Arcadi, S. Cacchi, F. Marinelli, and D. Misiti Tetrahedron Lett. 29 1988 1457 1460
142. L. Bleicher, and N.D.P. Cosford Synlett 1995 1115 1116
143. Y. Inoue, K. Ohuchi, S. Imaizumi, H. Hagiwara, and H. Uda Synth. Commun. 20 1990 3063 3068
144. N.A. Bumagin, A.B. Ponomaryov, and I.P. Beletskaya Synthesis 1984 728 729
145. T.J.J. Müller, R. Braun, and M. Ansorge Org. Lett. 2 2000 1967 1970
146. R.U. Braun, K. Zeitler, and T.J.J. Müller Org. Lett. 2 2000 4180 4184
147. R.U. Braun, K. Zeitler, and T.J.J. Müller Org. Lett. 3 2001 3297 3330
148. N.A.M. Yehia, K. Polborn, and T.J.J. Müller Tetrahedron Lett. 43 2002 6907 6910
149. R.U. Braun, and T.J.J. Müller Tetrahedron 60 2004 9463 9469
150. R.U. Braun, and T.J.J. Müller Synthesis 2004 2391 2406
151. D.M. D'Souza, F. Rominger, and T.J.J. Müller Angew. Chem. Int. Ed. 44 2005 153 158
152. M. Feuerstein, H. Doucet, and M. Santelli Tetrahedron Lett. 45 2004 1603 1606
153. M. Pal, K. Parasuraman, S. Gupta, and K.R. Yeleswarapu Synlett 2002 1976 1982
154. For the inefficiency of this catalytic coupling in the absence of a reoxidant, see: Z. Zhang, X. Lu, Z. Xu, Q. Zhang, and X. Han Organometallics 20 2001 3724 3728
155. D.E. Bergstrom, J.L. Ruth, and P. Warwick J. Org. Chem. 46 1981 1432 1441
156. U. Hacksell, and G.D. Daves Jr. J. Org. Chem. 48 1983 2870 2876
157. U. Hacksell, and G.D. Daves Jr. Organometallics 2 1983 772 775
158. J.C.-Y. Cheng, U. Hacksell, and G.D. Daves Jr. J. Org. Chem. 51 1986 3093 3098
159. G.D. Daves Jr. Acc. Chem. Res. 23 1990 201 206
160. G.D. Daves Jr. H. Ogura A. Hasegawa T. Suami Carbohydrates Synthetic Methods and Applications in Medicinal Chemistry 1992 Kodansha Ltd Tokyo 49 64
161. K. Matoba, S.-I. Motufusa, C.S. Cho, K. Ohe, and S. Uemura J. Organomet. Chem. 574 1999 3 10
162. M. Yoshida, T. Gotou, and M. Ihara Tetrahedron Lett. 45 2004 5573 5575
163. H. Narahashi, A. Yamamoto, and I. Shimizu Chem. Lett. 33 2004 348 349
164. T. Fuchikami, Y. Shibata, and H. Urata Chem. Lett. 1987 521 524
165. L. Shi, C.K. Narula, K.T. Mak, L. Kao, Y. Xu, and R.F. Heck J. Org. Chem. 48 1983 3894 3900
166. J.-M. Gaudin Tetrahedron Lett. 32 1991 6113 6116
167. S.A. Kelly, Y. Foricher, J. Mann, and J.M. Bentley Org. Biomol. Chem. 1 2003 2865 2876
168. K. Kondo, M. Sodeoka, M. Mori, and M. Shibasaki Tetrahedron Lett. 34 1993 4219 4222
169. K. Kondo, M. Sodeoka, M. Mori, and M. Shibasaki Synthesis 1993 920 930
170. G. Dyker, and P. Grundt Eur. J. Org. Chem. 1999 323 327
171. S.K. Mal, D. Ray, and J.K. Ray Tetrahedron Lett. 45 2004 277 279
172. Ray, J. K. Personal communications January, 2004.
173. J. Zhao, X. Yang, X. Jia, S. Luo, and H. Zhai Tetrahedron 59 2003 9379 9382
174. B.M. Trost, J.R. Corte, and M.S. Gudiksen Angew. Chem. Int. Ed. 38 1999 3662 3664
175. B.M. Trost, and R. Rise J. Am. Chem. Soc. 3161 1987 3163
176. 2 in refluxing benzene: B.M. Trost, and J.Y.L. Chung J. Am. Chem. Soc. 107 1985 4586 4588
177. 115
178. C.J. Kressierer, and T.J.J. Müller Synlett 2004 655 658
179. C.J. Kressierer, and T.J.J. Müller Tetrahedron Lett. 45 2004 2155 2158
180. 69,115
181. G. Zhu, and X. Lu Organometallics 14 1995 4899 4904
182. J.-P. Genêt, and F. Piau J. Org. Chem. 46 1981 2414 2417
183. J.-P. Genêt, M. Balabane, and Y. Legras Tetrahedron Lett. 23 1982 331 334
184. F.-P. Montforts, I. Gesing-Zibulak, W. Grammenos, M. Schneider, and K. Laumen Helv. Chim. Acta 72 1989 1852 1859
185. H.E. Schink, and J.-E. Bäckvall J. Org. Chem. 57 1992 1588 1591
186. F.A. Luzzio, A.V. Mayorov, and W.D. Figg Tetrahedron Lett. 41 2000 2275 2278
187. G. Poli, G. Giambastini, M. Malacria, and S. Thorimbert Tetrahedron Lett. 42 2001 6287 6289
188. B.M. Trost, and C.R. Self J. Org. Chem. 49 1984 468 473
189. K.E. Atkins, W.E. Walker, and R.M. Manyik Tetrahedron Lett. 1970 3821 3824
190. 127
191. J. Smidt, and W. Hafner Angew. Chem. 71 1959 284
192. T. Yamamoto, M. Akimoto, O. Saito, and A. Yamamoto Organometallics 5 1986 1559 1567
193. T. Hosokawa, T. Tsuji, Y. Mizumoto, and S.-I. Murahshi J. Organomet. Chem. 574 1999 99 101
194. F. Ozawa, T. Ishiyama, S. Yamamoto, S. Kawagishi, H. Murakami, and M. Yoshifuji Organometallics 23 2004 1698 1707
195. M. Moreno-Mañas, and A. Trius Tetrahedron 37 1981 3009 3015
196. J.-E. Bäckvall, R.E. Nordberg, J.-E. Nyström, T. Högberg, and B. Ulff J. Org. Chem. 46 1981 3479 3483
197. H. Bricourt, J.-F. Carpentier, and A. Mortreux J. Mol. Catal. A: Chem. 136 1998 243 251
198. Y. Masuyama, M. Kagawa, and Y. Kurusu Chem. Lett. 1995 1121 1122
199. D.E. Bergbreiter, B. Chen, and T.J. Lynch J. Org. Chem. 48 1983 4179 4186
200. Y. Tanigawa, K. Nishimura, A. Kawasaki, and S.-I. Murahashi Tetrahedron Lett. 23 1982 5549 5552
201. J. Que, Y. Ishimura, T. Oe, and N. Nagato Nippon Kagaku Kaishi 1996 250 255 Chem. Abstr. 1996, 180874
202. Ishimura, Y.; Kyoku, K.; Chiba, T. Jpn. Kokai Tokkyo Koho JP 04321655, 1992; Chem. Abstr. 1993, 213115.
203. J. Que, Y. Ishimura, and N. Nagato Nippon Kagaku Kaishi 1996 256 259 Chem. Abstr. 1996, 180875
204. Ishimura, Y.; Kyoku, K. Jpn. Kokai Tokkyo Koho JP 05058916, 1993; Chem. Abstr. 1993 471949.
205. J. Que, Y. Ishimura, and N. Nagato Nippon Kagaku Kaishi 1996 525 529 Chem. Abstr. 1996, 370001
206. Y. Kayaki, T. Koda, and T. Ikariya J. Org. Chem. 69 2004 2595 2597
207. F. Ozawa, H. Okamoto, S. Kawagishi, S. Yamamoto, T. Minami, and M. Yoshifuji J. Am. Chem. Soc. 124 2002 10968 10969
208. H. Liang, S. Ito, and M. Yoshifuji Org. Lett. 6 2004 425 427
209. B.M. Trost, and T.R. Verhoeven J. Am. Chem. Soc. 102 1980 4730 4743
210. (a) Haudegond, J.-P., Commereuc, D., Collin, J., Chauvin, Y. Fr. Demande FR 2474491, 1981; Chem. Abstr. 96, 85976.
211. J.-P. Haudegond, Y. Chauvin, and D. Commereuc J. Org. Chem. 44 1979 3063 3065
212. C. Siem de Sanchez, and O. Gelambi Acta Cientifica Venezolona 39 1988 319 322 Chem. Abstr. 112, 158880
213. D.E. Bergbreiter, and D.A. Weatherford J. Chem. Soc., Chem. Commun. 1989 883 884
214. M. Sakakibara, and A. Ogawa Tetrahedron Lett. 43 1994 8013 8014
215. 145
216. D.E. Bergbreiter, and D.A. Weatherford J. Org. Chem. 54 1989 2726 2730
217. A. Hosokawa, and K. Yoshida Synthesis 2003 1321 1323
218. 139 According to Ikariya et al., this can be due to the facile coordination of this acyclic 1,3-dicarbonyl compound to the Pd center, leading to the inhibition of the catalyst.
219. J. Tsuji, I. Shimizu, I. Minami, Y. Ohashi, T. Sugiura, and K. Takahashi J. Org. Chem. 50 1985 1523 1529
220. P. Aleksandrowicz, H. Piotrowska, and W. Sas Tetrahedron 38 1982 1321 1327
221. J.B. Baruah, and A.G. Samuelson J. Organomet. Chem. 361 1989 C57 C60
222. X. Lu, and L. Lu J. Organomet. Chem. 307 1986 285 289
223. X. Lu, L. Lu, and J. Sun J. Mol. Catal. 41 1987 245 251
224. X. Lu, X. Jiang, and X. Tao J. Organomet. Chem. 344 1988 109 118
225. 155 this allylation has already been described using allyl acetate: D. Ferroud, J.-P. Genêt, and J. Muzart Tetrahedron Lett. 25 1984 4379 4382
226. I. Starý, I.G. Stará, and P. Kočovský Tetrahedron Lett. 34 1983 179 182
227. I. Starý, I.G. Stará, and P. Kočovský Tetrahedron 50 1994 529 537
228. S.-C. Yang, and C.-W. Hung J. Org. Chem. 64 1999 5000 5001
229. S.-C. Yang, C.-L. Yu, and Y.-C. Tsai Tetrahedron Lett. 41 2000 7097 7100
230. S.-C. Yang, and C.-W. Hung Organometallics 21 2002 2013 2016
231. S.-C. Yang, and C.-W. Hung Synthesis 1999 1747 1752
232. S.-C. Yang, and C.-W. Hung Tetrahedron Lett. 40 1999 953 956
233. S.-C. Yang, and Y.-C. Tsai Organometallics 20 2002 763 770
234. Y.-J. Shue, S.-C. Yang, and H.-C. Lai Tetrahedron Lett. 44 2003 1481 1485
235. S.-C. Yang, H.-C. Lai, and Y.-C. Tsai Tetrahedron Lett. 45 2004 2693 2697
236. Y. Tamaru, Y. Horino, M. Araki, S. Tanaka, and M. Kimura Tetrahedron Lett. 41 2000 5705 5709
237. Y. Horino, M. Naito, M. Kimura, S. Tanaka, and Y. Tamaru Tetrahedron Lett. 42 2001 3113 3116
238. M. Kimura, M. Futamata, K. Shibata, and Y. Tamaru Chem. Commun. 2003 234 235
239. M. Kimura, R. Mukai, N. Tanigawa, S. Tanaka, and Y. Tamaru Tetrahedron 59 2003 7767 7777
240. J.M. Takacs, X.-T. Jiang, and A.P. Leonov Tetrahedron Lett. 44 2003 7075 7079
241. M. Kimura, Y. Horino, R. Mukai, S. Tanaka, and Y. Tamaru J. Am. Chem. Soc. 123 2001 10401 10402
242. R. Mukai, Y. Horino, S. Tanaka, Y. Tamaru, and M. Kimura J. Am. Chem. Soc. 126 2004 11138 11139
243. K. Itoh, N. Hamaguchi, M. Miura, and M. Nomura J. Chem. Soc., Perkin Trans. 1 1992 2833 2835
244. T.K.M. Shing, L.-H. Li, and K. Narkunan J. Org. Chem. 62 1997 1617 1622
245. R. Kumareswaran, and Y.D. Vankar Tetrahedron Lett. 38 1997 8421 8424
246. Tokito, Y. Jpn. Kokai Tokkyo Koho JP 04208233, 1992; Chem. Abstr. 118, 38461.
247. M. Sakamoto, I. Shimizu, and A. Yamamoto Bull. Chem. Soc. Jpn. 69 1996 1065 1078
248. S.-I. Murahashi, T. Shimahura, and I. Moritani Chem. Commun. 1974 931 932
249. Y. Yokoyama, H. Hikawa, M. Mitsuhashi, A. Uyama, Y. Hiroki, and Y. Murakami Tetrahedron Lett. 40 1999 7803 7806
250. Y. Yokoyama, H. Hikawa, M. Mitsuhashi, A. Uyama, Y. Hiroki, and Y. Murakami Eur. J. Org. Chem. 2004 1244 1253
251. Rabeyrin C. Ph.D. Thesis Lyon, 2003.
252. K. Manabe, and S. Kobayashi Org. Lett. 5 2003 3241 3244
253. Kobayashi, O., Manabe, T. Jpn. Kokai Tokkyo Koho JP 262,843, 2004; Chem. Abstr. 141, 277355.
254. N.T. Patil, and Y. Yamamoto Tetrahedron Lett. 45 2004 3101 3103
255. H. Kinoshita, H. Shinokubo, and K. Oshima Org. Lett. 6 2004 4085 4088
256. T. Hayashi, M. Konishi, and M. Kumada J. Organomet. Chem. 186 1980 C1 C4
257. T. Hayashi, M. Konishi, K. Yokota, and M. Kumada J. Chem. Soc., Chem. Commun. 1981 313 314
258. T. Hayashi, M. Konishi, K. Yokota, and M. Kumada J. Organomet. Chem. 285 1985 359 373
259. H. Tsukamoto, M. Sato, and Y. Kondo Chem. Commun. 2004 1200 1201
260. Y. Kayaki, T. Koda, and T. Ikariya Eur. J. Org. Chem. 2004 4989 4993
261. (b) Kayanoki, H.; Ikariya, T. Jpn. Kokai Tokkyo Koho JP 2004 91, 405, 2004; Chem. Abstr. 140, 270549.
262. M. Yoshida, T. Gotou, and M. Ihara Chem. Commun. 2004 1124 1125
263. This mechanistic scheme is slightly different from the authors one which depicted only σ-allylpalladium intermediates.
264. For a review of unpolung reactions involving organopalladium intermediates, see: J.A. Marshall Chem. Rev. 100 2000 3163 3185
265. Y. Masuyama, J.P. Takahara, and Y. Kurusu J. Am. Chem. Soc. 110 1988 4473 4474
266. Y. Masuyama, J.P. Takahara, and Y. Kurusu Tetrahedron Lett. 30 1989 3437 3440
267. J.P. Takahara, Y. Masuyama, and Y. Kurusu J. Am. Chem. Soc. 114 1992 2577 2586
268. Y. Masuyama, R. Hayashi, K. Otake, and Y. Kurusu J. Chem. Soc., Chem. Commun. 1988 44 45
269. Y. Masuyama, Y. Nimura, and Y. Kurusu Tetrahedron Lett. 32 1991 225 228
270. Y. Masuyama, T. Tsunoda, and Y. Kurusu Chem. Lett. 1989 1647 1650
271. Y. Masuyama, A. Hayakawa, and Y. Kurusu J. Chem. Soc., Chem. Commun. 1992 1102 1103
272. Y. Masuyama, S. Mochizuki, and Y. Kurusu Synth. Commun. 27 1997 1015 1021
273. T. Okano, J. Kiji, and T. Doi Chem. Lett. 1998 5 6
274. L. Carde, A. Llebaria, and A. Delgado Tetrahedron Lett. 42 2001 3299 3302
275. X.-H. Tan, Y.-Q. Hou, B. Shen, L. Liu, and Q.-X. Guo Tetrahedron Lett. 45 2004 5525 5528
276. M. Kimura, M. Shimizu, K. Shibata, M. Tazoe, and Y. Tamaru Angew. Chem. Int. Ed. 42 2003 3392 3395
277. M. Kimura, T. Tomizawa, Y. Horino, S. Tanaka, and Y. Tamaru Tetrahedron Lett. 41 2000 3627 3629
278. S. Araki, T. Kamei, T. Hirashita, H. Yamamura, and M. Kawai Org. Lett. 2 2000 847 849
279. Fontana, G.; Lubineau, A.; Scherrmann, M. -C. Unpublished results.
280. T.-S. Jang, G. Keum, S.B. Kang, B.Y. Chung, and Y. Kim Synthesis 2003 775 779
281. M. Moreno-Mañas, and A. Trius Tetrahedron Lett. 22 1981 3109 3112
282. M. Moreno-Mañas, and A. Trius Bull. Chem. Soc. Jpn. 56 1983 2154 2158
283. M. Moreno-Mañas, R.M. Ortuño, M. Prat, and M.A. Galán Synth. Commun. 16 1986 1003 1013
284. The formation of the allylphosphonium directly from the allylic alcohol and the phosphine could be also envisaged: C.-W. Cho, J.-R. Kong, and M.J. Krische Org. Lett. 6 2004 1337 1339
285. N. Okukada, O. Uchikawa, and Y. Nakamura Chem. Lett. 1988 1449 1452
286. T. Zair, C. Santelli-Rouvier, and M. Santelli Tetrahedron Lett. 32 1991 4501 4502
287. T. Zair, C. Santelli-Rouvier, and M. Santelli Tetrahedron 49 1991 3313 3324
288. N. Tsukada, T. Sato, and Y. Inoue Chem. Commun. 2003 2404 2405
289. D.J. Cárdenas, M. Alcami, F. Cossío, M. Méndez, and A.M. Echavarren Chem. Eur. J. 9 2003 96 105
290. N. Tsukuda, S. Sugawara, K. Nakaoka, and Y. Inoue J. Org. Chem. 68 2003 5961 5966
291. N. Tsukuda, S. Sugawara, and Y. Inoue Org. Lett. 2 2000 655 657
292. H. Nakamura, K. Aoyagi, J.-G. Shim, and Y. Yamamoto J. Am. Chem. Soc. 123 2001 372 377
293. 2Pd has a nucleophilic character and acts as an amphiphilic agent towards certain Michael acceptors: (a) H. Nakamura, J.-G. Shim, and Y. Yamamoto J. Am. Chem. Soc. 119 1997 8113 8114
294. N. Solin, S. Narayan, and K.J. Szabó J. Org. Chem. 66 2001 1686 1693
295. N. Solin, S. Narayan, and K.J. Szabó Org. Lett. 3 2001 909 912
296. K. Szabó Chem. Eur. J. 10 2004 5268 5275
297. H. Hiemstra, and R.A.T.M. van Benthem Bull. Soc. Chim. Belg. 103 1994 559 563
298. P.J. Harrington, L.S. Hegedus, and K.F. McDaniel J. Am. Chem. Soc. 109 1987 4335 4338
299. 101,110,122
300. 215
301. S. Saito, T. Hara, N. Takahashi, M. Hirai, and T. Morikawe Synlett 1992 237 238
302. M. Kimura, H. Harayama, S. Tanaka, and Y. Tamaru J. Chem. Soc., Chem. Commun. 1994 2531 2533
303. Y. Tamaru, T. Kobayashi, S. Kawamura, H. Ochiai, and Z. Yoshida Tetrahedron Lett. 26 1985 4479 4482
304. Y. Tamaru, and Z. Yoshida J. Organomet. Chem. 334 1987 213 223
305. Y. Tamaru, M. Hojo, and Z. Yoshida J. Org. Chem. 53 1988 5731 5741
306. V. Jäger, and W. Hümmer Angew. Chem., Int. Ed. Engl. 29 1990 1171 1173
307. W. Hümmer, E. Dubois, T. Gracza, and V. Jäger Synthesis 1997 634 642
308. P. Szolcsányi, T. Gracza, M. Koman, N. Prónayová, and T. Liptaj Chem. Commun. 2000 471 472
309. V. Jäger, T. Gracza, E. Dubois, T. Hasenöhrl, W. Hümmer, B.K. Kautz, A. Lieberknecht, L. Remen, D. Shaw, U. Stahl, and O. Stephan G. Helmchen J. Dibo D. Flubacher B. Wiese Organic Synthesis via Organometallics, OSM 5 1997 Vieweg Braunschweig 331 360
310. Y. Hirai, and M. Nagatsu Chem. Lett. 1994 21 22
311. Y. Hirai, K. Shibuya, Y. Fukuda, H. Yokoyama, and S. Yamaguchi Chem. Lett. 1997 221 222
312. H. Yokoyama, K. Otaya, S. Yamaguchi, and Y. Hirai Tetrahedron Lett. 39 1998 5971 5974
313. H. Yokoyama, K. Otaya, H. Kobayashi, M. Miyazawa, S. Yamaguchi, and Y. Hirai Org. Lett. 2 2000 2427 2429
314. H. Makabe, L.K. Kong, and M. Hirota Org. Lett. 5 2003 27 29
315. K. Utimoto, H. Miwa, and H. Nozaki Tetrahedron Lett. 22 1981 4277 4278
316. K. Utimoto Pure Appl. Chem. 55 1983 1845 1852
317. M. Shimizu, M. Kimura, T. Watanabe, and Y. Tamaru Organic Lett. 7 2005 637 640
318. S.A. Forsyth, H.Q. Gunaratne, C. Hardcare, A. McKeown, D.W. Rooney, and K.R. Seddon J. Mol. Catal. A: Chem. 231 2004 61 66