β-Elimination competitions leading to C=C bonds from alkylpalladium intermediates

Tetrahedron

Volumn 68, Issue 49, 2012, Pages 10065-10113

  Le Bras, Jean ^a   Muzart, Jacques ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Aza Wacker reaction; Elimination; Heck reaction; Heterocyclisation; Palladium; Selectivity; Wacker reaction

Indexed keywords

ACETAL DERIVATIVE; ACROLEIN; ALCOHOL DERIVATIVE; ALKENE; ALKYL GROUP; ALLYL ALCOHOL; AMINE; CARBAMIC ACID; CARBON; CARBONIC ACID; ESTER; ETHER; HALIDE; HYDROGEN; HYDROXYL GROUP; PALLADIUM; SILANE DERIVATIVE; SULFONE DERIVATIVE; TRICHLOROACETIMIDIC ACID; VINYL ACETATE;

ADDITION REACTION; ALKYLATION; ARYLATION; BETA ELIMINATION REACTION; CARBON BOND; CHEMICAL BOND; CIS TRANS ISOMERISM; CYCLIZATION; ELIMINATION REACTION; HYDROGEN BOND; ISOMERIZATION; MOLECULAR DYNAMICS; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; STOICHIOMETRY; TAUTOMERIZATION;

EID: 84867876289     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.09.076     Document Type: Review

References (304)

1. M. Oestreich The Mizoroki-Heck Reaction 2009 Wiley Chichester, UK
2. S.G. Davies Organotransition Metal Chemistry: Applications to Organic Synthesis 1982 Pergamon Oxford, UK
3. L.S. Hegedus Transition Metals in the Synthesis of Complex Organic Molecules 1994 University Science Books Mill Valley
4. J.M. Campagne, and D. Prim Les complexes du palladium en synthèse organique 2001 CNRS Editions Paris
5. G. Zeni, and R.C. Larock Chem. Rev. 104 2004 2285 2309
6. J. Tsuji Palladium Reagents and Catalysts 2004 Wiley Chichester, UK 15
7. H. Zhao, A. Ariafard, and Z. Lin Organometallics 25 2006 812 819
8. G. Zhu, and X. Lu Organometallics 14 1995 4899 4904
9. Z. Zhang, X. Lu, Z. Xu, Q. Zhang, and X. Han Organometallics 20 2001 3724 3728
10. J. Tsuji Palladium Reagents and Catalysts 2004 Wiley Chichester, UK 494-499
11. J. Muzart Eur. J. Org. Chem. 2011 4717 4741 For reports concerning syn and anti hydride eliminations via such reactions, see
12. T. Takahashi, N. Nakagawa, T. Minoshima, H. Yamada, and J. Tsuji Tetrahedron Lett. 31 1990 4333 4336
13. J.M. Takacs, E.C. Lawson, and F. Clement J. Am. Chem. Soc. 119 1997 5956 5957
14. P.G. Andersson, and S. Schab Organometallics 14 1995 1 2
15. I. Schwarz, and M. Braun Chem. - Eur. J. 5 1999 2300 2305
16. For a review, see: J. Muzart Eur. J. Org. Chem. 2010 3779 3790
17. J. Tsuji Tetrahedron 42 1986 4361 4401
18. J. Tsuji, and I. Minami Acc. Chem. Res. 20 1987 140 145
19. J. Tsuji Palladium Reagents and Catalysts 2004 Wiley Chichester, UK 500-506
20. J. Tsuji, M. Nisar, and I. Minami Tetrahedron Lett. 27 1986 2483 2486
21. J. Tsuji, M. Nisar, and I. Minami Chem. Lett. 1987 23 24
22. R.F. Heck J. Am. Chem. Soc. 90 1968 5535 5542
23. For the formation of a five-membered palladacycle from the chelation of an acetate group to palladium, see: B.S. Williams, M.D. Leatherman, P.S. White, and M. Brookhart J. Am. Chem. Soc. 127 2005 5132 5146
24. A. Kasahara, T. Izumi, and N. Fukuda Bull. Chem. Soc. Jpn. 50 1977 551 552
25. M. Lautens, E. Tayama, and C. Herse J. Am. Chem. Soc. 127 2005 72 73
26. J. Muzart J. Mol. Catal. A: Chem. 308 2009 15 24
27. K. Kikuwa, M. Naritomi, G.-X. He, F. Wada, and T. Matsuda J. Org. Chem. 50 1985 299 301
28. B.M. Choudary, and M. Ravichandra Sarma Tetrahedron Lett. 31 1990 1495 1496
29. I. Arai, and G.D. Daves Jr. J. Org. Chem. 44 1979 21 23
30. D. Pan, and N. Jiao Synlett 2010 1577 1588
31. J.C.Y. Cheng, and G.D. Daves Jr. Organometallics 5 1986 1753 1755
32. G.D. Daves Jr. Acc. Chem. Res. 23 1990 201 206
33. C. Munro-Leighton, L.L. Adduci, J.J. Becker, and M.R. Gagné Organometallics 30 2011 2646 2649
34. B. Mariampillai, C. Herse, and M. Lautens Org. Lett. 7 2005 4745 4747
35. Y. Liu, B. Yao, C.L. Deng, R.Y. Tang, X.G. Zhang, and J.H. Li Org. Lett. 13 2011 1126 1129
36. H.A. Dieck, and R.F. Heck J. Org. Chem. 40 1975 1083 1090
37. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457 2483
38. M. Moreno-Mañas, M. Pérez, and R. Pleixats J. Org. Chem. 61 1996 2346 2351
39. J. Ramnauth, O. Poulin, S. Rakhit, and S.P. Maddaford Org. Lett. 3 2001 2013 2015
40. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009 3066
41. H. Ohmiya, Y. Makida, T. Tanaka, and M. Sawamura J. Am. Chem. Soc. 130 2008 17276 17277
42. H. Ohmiya, Y. Makida, D. Li, M. Tanabe, and M. Sawamura J. Am. Chem. Soc. 132 2010 879 889
43. Y. Makida, H. Ohmiya, and M. Sawamura Chem. Asian J. 6 2011 410 414
44. B. Yao, Y. Liu, M.K. Wang, J.H. Li, R.Y. Tang, X.G. Zhang, and C.L. Deng Adv. Synth. Catal. 354 2012 1069 1076
45. Q. Zhang, X. Lu, and X. Han J. Org. Chem. 66 2001 7676 7684
46. P.M. Henry Acc. Chem. Res. 6 1973 16 24
47. S. Aït-Mohand, F. Hénin, and J. Muzart Organometallics 20 2001 1683 1686
48. Q. Zhang, W. Xu, and X. Lu J. Org. Chem. 70 2005 1505 1507
49. Q. Zhang, and X. Lu J. Am. Chem. Soc. 122 2000 7604 7605
50. D. Pan, A. Chen, Y. Su, W. Zhou, S. Li, W. Jia, J. Xiao, Q. Liu, L. Zhang, and N. Jiao Angew. Chem., Int. Ed. 47 2008 4729 4732
51. W. Chen, M. Xu, D.L. Bo, and N. Jiao Chin. J. Org. Chem. 30 2010 469 473
52. N.M. Evdokimov, A. Kornienko, and I.V. Magedov Tetrahedron Lett. 52 2011 4327 4329
53. J. Wang, Z. Cui, Y. Zhang, H. Li, L.M. Wu, and Z. Liu Org. Biomol. Chem. 9 2011 663 666
54. Liu, Z. Personal communication on the structure of 2-(2,4,5- trimethoxybenzyl)allyl acetate, April 13, 2011.
55. Y. Zhang, Z. Li, and Z.Q. Liu Org. Lett. 14 2012 226 229
56. T. Mino, T. Koizumi, S. Suzuki, K. Hirai, K. Kajiwara, M. Sakamoto, and T. Fujita Eur. J. Org. Chem. 2012 678 680
57. Y. Su, and N. Jiao Org. Lett. 11 2009 2980 2983
58. T.W. Hudnall, C.W. Chiu, and F.P. Gabbai Acc. Chem. Res. 42 2009 388 397
59. D.L. Davies, S.M.A. Donald, and S.A. Macgregor J. Am. Chem. Soc. 127 2005 13754 13755
60. I. Ambrogio, G. Fabrizi, S. Cacchi, S.T. Henriksen, P. Fristrup, D. Tanner, and P.O. Norrby Organometallics 27 2008 3187 3195
61. A.V. Moro, F.S.P. Cardoso, and C.R.D. Correia Org. Lett. 11 2009 3642 3645
62. C. Soldi, A.V. Moro, M.G. Pizzolatti, and C.R.D. Correia Eur. J. Org. Chem. 2012 3607 3616
63. For a review on dehydrogenative Heck reactions, see: J. Le Bras, and J. Muzart Chem. Rev. 111 2011 1170 1214
64. X. Shang, Y. Xiong, Y. Zhang, L. Zhang, and Z. Liu Synlett 2012 259 262
65. D. Pan, M. Yu, W. Chen, and N. Jiao Chem. Asian J. 5 2010 1090 1093
66. A. Kubota, M.H. Emmert, and M.S. Sanford Org. Lett. 14 2012 1760 1763
67. Z. Li, Y. Zhang, and Z.Q. Liu Org. Lett. 14 2012 74 77
68. Y. Zhang, Z. Cui, Z. Li, and Z.Q. Liu Org. Lett. 14 2012 1838 1841
69. J.H. Delcamp, and M.C. White J. Am. Chem. Soc. 128 2006 15076 15077
70. J. Ruan, X. Li, O. Saidi, and J. Xiao J. Am. Chem. Soc. 130 2008 2424 2425
71. II species, see: W. Cabri, and I. Candiani Acc. Chem. Res. 28 1995 2 7
72. J.F. Harrod, and A.J. Chalk J. Am. Chem. Soc. 86 1964 1776 1779
73. D. Bingham, B. Hudson, D.E. Webster, and P.B. Wells J. Chem. Soc., Dalton Trans. 1974 1521 1524
74. S. Xiang, S. Cai, J. Zeng, and X.W. Liu Org. Lett. 13 2011 4608 4611
75. Muzart, J. Tetrahedron 2005, 61, 4179e4212
76. J. Tsuji Palladium Reagents and Catalysts, Innovations in Organic Synthesis 1995 Wiley Chichester, UK 127. A number of reports concern however Heck-type cyclisations arising via the formal anti β-H elimination; for a review, see
77. M. Ikeda, S.A.A. El Bialy, and T. Yakura Heterocycles 51 1999 1957 1970 see also
78. K.M. Shea, K.L. Lee, and R.L. Danheiser Org. Lett. 2 2000 2353 2356
79. M. Lautens, and Y.Q. Fang Org. Lett. 5 2003 3679 3682
80. R. Imbos, A.J. Minnaard, and B.L. Feringa Dalton Trans. 2003 2017 2023 and the references cited in these reports. For a recent intermolecular reaction involving the formal anti β-H elimination, see
81. H.Y. Fu, L. Chen, and H. Doucet J. Org. Chem. 77 2012 4473 4478
82. E.W. Werner, K.B. Urkalan, and M.S. Sigman Org. Lett. 12 2010 2848 2851
83. E.W. Werner, and M.S. Sigman J. Am. Chem. Soc. 133 2011 9692 9695
84. T. Hosokawa, T. Sugafuji, T. Yamanaka, and S.-I. Murahashi J. Organomet. Chem. 470 1994 253 255
85. X. Lu Top. Catal. 35 2005 73 86
86. U. Hacksell, and G.D. Daves Jr. Organometallics 2 1983 772 775
87. J.M. Huang, L. Zhou, and H.F. Jiang Angew. Chem., Int. Ed. 45 2006 1945 1949
88. For the dependence of the stereochemistry of the halopalladation of triple bonds with the experimental conditions, see: G. Zhu, and X. Lu J. Organomet. Chem. 508 1996 83 90
89. H. Jiang, C. Qiao, and W. Liu Chem. - Eur. J. 16 2010 10968 10970
90. F. Wang, S. Li, M. Qu, M.-X. Zhao, L.-J. Liu, and M. Shi Chem. Commun. 2011 12813 12815
91. J. Muzart Tetrahedron 61 2005 4179 4212
92. J. Le Bras, and J. Muzart Synthesis 2011 3581 3591
93. J.B. Melpolder, and R.F. Heck J. Org. Chem. 41 1976 265 272
94. A.J. Chalk, and S.A. Magennis J. Org. Chem. 41 1976 273 278
95. R.F. Heck Organotransition Metal Chemistry 1974 Academic New York, NY pp 105-106
96. W. Smadja, G. Ville, and G. Cahiez Tetrahedron Lett. 25 1984 1793 1796
97. W. Smadja, S. Czernecki, G. Ville, and C. Georgoulis Organometallics 6 1987 166 169
98. Y. Wen, L. Huang, H. Jiang, and H. Chen J. Org. Chem. 77 2012 2029 2034
99. A.M. Zawisza, B. Ganchegui, I. González, S. Bouquillon, A. Roglans, F. Hénin, and J. Muzart J. Mol. Catal. A: Chem. 283 2008 140 145
100. J.A. Keith, J. Oxgaard, and W.A. Goddard III J. Am. Chem. Soc. 128 2006 3132 3133
101. J.A. Keith, and P.M. Henry Angew. Chem., Int. Ed. 48 2009 9038 9049
102. J.E. Bäckvall, B. Åkermark, and S.O. Ljunggren J. Am. Chem. Soc. 101 1979 2411 2416
103. R.H. Crabtree The Organometallic Chemistry of the Transition Metals 2nd ed. 1994 Wiley New York, NY 195
104. K. Kikukawa, K. Nagira, F. Wada, and T. Matsuda Tetrahedron 37 1981 31 36
105. J. Masllorens, S. Bouquillon, A. Roglans, F. Hénin, and J. Muzart J. Organomet. Chem. 690 2005 3822 3826
106. R. Perez, D. Veronese, F. Coelho, and O.A.C. Antunes Tetrahedron Lett. 47 2006 1325 1328
107. M. Barbero, S. Cadamuro, and S. Dughera Synthesis 2006 3443 3452
108. E. Bernocchi, S. Cacchi, P.G. Ciattini, E. Morera, and G. Ortar Tetrahedron Lett. 33 1992 3073 3076
109. M. Zhu, Y. Song, and Y. Cao Synthesis 2007 853 856
110. T. Jeffery J. Chem. Soc., Chem. Commun. 1991 324 325
111. T. Jeffery Tetrahedron Lett. 32 1991 2121 2124
112. T. Jeffery Tetrahedron Lett. 34 1993 1133 1136
113. B.M. Trost, J.R. Corte, and M.S. Gudiksen Angew. Chem., Int. Ed. 38 1999 3662 3664 In footnote 19, the authors noted that the effect of silver salts on the H elimination selectivity is opposite to that normally observed
114. T. Jeffery Tetrahedron Lett. 31 1990 6641 6644
115. T. Jeffery J. Chem. Soc., Chem. Commun. 1984 1287 1289
116. A. Heim-Riether Synthesis 2008 883 886
117. M. van de Sande, and H.J. Gais Chem. - Eur. J. 13 2007 1784 1795
118. V. Calò, A. Nacci, A. Monopoli, and V. Ferola J. Org. Chem. 72 2007 2596 2601
119. N.S.C.R. Kumar, I.V.P. Raj, and A. Sudalai J. Mol. Catal. A: Chem. 269 2007 218 224
120. J. Krishna, A.G.K. Reddy, B.V. Ramulu, L. Mahendar, and G. Satyanarayana Synlett 2012 375 380
121. W. Cabri, I. Candiani, A. Bedeschi, and R. Santi J. Org. Chem 57 1992 3558 3563
122. J.P. Knowles, and A. Whiting Org. Biomol. Chem. 5 2007 31 44
123. A. Jutand M. Oestreich, The Mizoroki-Heck Reaction 2009 Wiley Chichester, UK 1 50
124. F. Proutiere, and F. Schoenebeck Synlett 2012 645 648
125. S.K. Kang, H.W. Lee, S.B. Jang, T.H. Kim, and S.J. Pyun J. Org. Chem. 61 1996 2604 2605
126. I. Ambrogio, S. Cacchi, G. Fabrizi, A. Goggiamani, and S. Sgalla Synlett 2009 620 624
127. J. Muzart Tetrahedron 59 2003 5789 5816
128. M. Hayashi Organometallic News 2003 40 45 Chem. Abstr., 139, 133050
129. B.M. Stoltz Chem. Lett. 33 2004 362 367
130. B.-Z. Zhan, and A. Thompson Tetrahedron 60 2004 2917 2935
131. T. Nishimura, and S. Uemura Synlett 2004 201 216
132. S.S. Stahl Angew. Chem., Int. Ed. 43 2004 3400 3420
133. M.E. Sigman, and D.R. Jensen Acc. Chem. Res. 39 2006 221 229
134. K. Kaneda, K. Ebitani, T. Mizugaki, and K. Mori Bull. Chem. Soc. Jpn. 79 2006 981 1016
135. C. Parmeggiani, and F. Cardona Green. Chem. 14 2012 547 564
136. A.A. Sabino, A.H.L. Machado, C.R.D. Correia, and M.N. Eberlin Angew. Chem., Int. Ed. 43 2004 2514 2518
137. A. Roglans, A. Pla-Quintana, and M. Moreno-Mañas Chem. Rev. 106 2006 4622 4643
138. J.G. Taylor, A.V. Moro, and C.R.D. Correia Eur. J. Org. Chem. 2011 1403 1428
139. F.-X. Felpin, L. Nassar-Hardy, F. Le Callonnec, and E. Fouquet Tetrahedron 67 2011 2815 2831
140. I.P. Beletskaya, and A.V. Cheprakov M. Oestreich, The Mizoroki-Heck Reaction 2009 Wiley Chichester, UK 59) which, at the present time, remains unsolved
141. Roglans, A. Personal communication, February 14, 2012.
142. B. Chen, X. Xie, J. Lu, Q. Wang, Q. Zhang, S. Tang, X. She, and X. Pan Synlett 2006 259 262
143. M. Chen, J. Wang, Z. Chai, C. You, and A. Lei Adv. Synth. Catal. 354 2012 341 346
144. J.M. Ku, B.S. Jeong, S. Jew, and H. Park J. Org. Chem. 72 2007 8115 8118
145. Y. Yokoyama, T. Matsumoto, and Y. Murakami J. Org. Chem. 60 1995 1486 1487
146. F. Berthiol, H. Doucet, and M. Santelli Appl. Organomet. Chem. 20 2006 855 868
147. T. Patonay, A. Vasas, A. Kiss-Szikszai, A.M.S. Silva, and J.A.S. Cavaleiro Aust. J. Chem. 63 2010 1582 1593
148. A. Vasas, T. Patonay, K. Kónya, A.M.S. Silva, and J.A.S. Cavaleiro Aust. J. Chem. 64 2011 647 657
149. S. Fekete, T. Patonay, A.M.S. Silva, and J.A.S. Cavaleiro Arkivoc v 2012 210 225
150. Arylation and alkenylation of tertiary allyl alcohols can lead to epoxides through the suspected intramolecular addition of the aryl(or alkenyl)palladium alcoholate to the CC bond: S. Hayashi, H. Yorimitsu, and K. Oshima J. Am. Chem. Soc. 131 2009 2052 2053
151. Other allylic alcohols can also lead to epoxides, but this would be restricted to the reaction with polyfluoralkyl halides under basic conditions; the addition of the polyfluoralkylpalladium halide to the CC bond was thus proposed: T. Fuchikami, Y. Shibata, and H. Urata Chem. Lett. 1987 521 524
152. A. Sauza, J.A. Morales-Serna, M. García-Molina, R. Gaviño, and J. Cárdenas Synthesis 2012 272 282
153. A. Hallberg, L. Westfelt, and B. Holm J. Org. Chem. 46 1981 5414 5415
154. M. Larhed, C.-M. Andersson, and A. Hallberg Tetrahedron 50 1994 285 304
155. C.-M. Andersson, and A. Hallberg J. Org. Chem. 54 1989 1502 1505
156. D.S. Gaikwad, Y. Park, and D.M. Pore Tetrahedron Lett. 53 2012 3077 3081
157. T. Jeffery, and M. David Tetrahedron Lett. 39 1998 5751 5754
158. M.O. Fitzpatrick, H. Muller-Bunz, and P.J. Guiry Eur. J. Org. Chem. 2009 1889 1895
159. M. Kishida, and H. Akita Tetrahedron 61 2005 10559 10568
160. F. Berthiol, M. Doucet, and M. Santelli Eur. J. Org. Chem. 2005 1367 1377
161. Z. Zhou, Y. Xie, Z. Du, Q. Hu, J. Xue, and J. Shi Arkivoc vi 2012 164 172
162. X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H.F. Wang, K. Fugami, and M. Kosugi Org. Lett. 3 2001 3313 3316
163. J. Nokami, A. Furukawa, Y. Okuda, A. Hazato, and S. Kurozumi Tetrahedron Lett. 39 1998 1005 1008
164. J.H. Delcamp, A.P. Brucks, and M.C. White J. Am. Chem. Soc. 130 2008 11270 11271
165. For the required precautions to interpret the deuterium kinetic isotope effects, see: E.M. Simmons, and J.F. Hartwig Angew. Chem., Int. Ed. 51 2012 3066 3072
166. A.G. Myers, D. Tanaka, and M.R. Mannion J. Am. Chem. Soc. 124 2002 11250 11251
167. D. Tanaka, S.P. Romeril, and A.G. Myers J. Am. Chem. Soc. 127 2005 10323 10333
168. T.T. Wenzel J. Chem. Soc., Chem. Commun. 1993 862 864
169. K. Awasaguchi, M. Miyazawa, I. Uoya, K. Inoue, K. Nakamura, H. Yokoyama, H. Kakuda, and Y. Hirai Synlett 2010 2392 2396
170. T.C. Zebovitz, and R.F. Heck J. Org. Chem. 42 1977 3907 3909
171. S.G. Davies, B.E. Mobbs, and C.J. Goodwin J. Chem. Soc., Perkin Trans. 1 1987 2597 2604
172. Experimental conditions for the selective arylation at the central carbon of acrolein diethyl acetal have been recently disclosed: L. Qin, X. Ren, Y. Lu, Y. Li, and J. Zhou Angew. Chem., Int. Ed. 51 2012 5915 5919
173. G. Battistuzzi, S. Cacchi, and G. Fabrizi Org. Lett. 5 2003 777 780
174. G. Battistuzzi, S. Cacchi, G. Fabrizi, and R. Bernini Synlett 2003 1133 1136
175. T. Hosokawa, H. Okhata, and I. Moritani Bull. Chem. Soc. Jpn. 48 1975 1533 1536
176. R.C. Larock, L. Wei, and T.R. Hightower Synlett 1998 522 524
177. For the similar dependence for the cyclisation of methyl 2-allyl-4,5,6-tribromo-3-hydroxybenzoate, see: F.A. Khan, and L. Soma Tetrahedron Lett. 48 2007 85 88
178. T. Hosokawa, S. Miyagi, S. Murahashi, and A. Sonoda J. Org. Chem. 43 1978 2752 2757
179. R.A.T.M. Van Benthem, H. Hiemstra, J.J. Michels, and W.N. Speckamp J. Chem. Soc., Chem. Commun. 1994 357 361
180. R.A.T.M. Van Benthem, H. Hiemstra, PW.N.M. van Leeuwen, J.W. Geus, and W.N. Speckamp Angew. Chem., Int. Ed. Engl. 34 1995 457 460
181. R.A.T.M. Van Benthem, H. Hiemstra, and W.N. Speckamp J. Org. Chem. 57 1992 6083 6085
182. J.-F. Nguefack, V. Bolitt, and D. Sinou J. Org. Chem. 62 1997 1341 1347
183. K. Bedjeguelal, V. Bolitt, and D. Sinou Synlett 1999 762 764
184. B. Alcaide, P. Almendros, T. Martíez del Campo, E. Soriano, and J.L. Marco-Contelles Chem. - Eur. J. 15 2009 1909 1928
185. B. Alcaide, P. Almendros, T. Martiez del Campo, E. Soriano, and J.L. Marco-Contelles Chem. - Eur. J. 15 2009 9127 9138
186. R.F. Heck J. Am. Chem. Soc. 90 1968 5531 5534
187. S.R. Foley, R.A. Stockland Jr., H. Shen, and R.F. Jordan J. Am. Chem. Soc. 125 2003 4350 4361
188. D.E. Bergstrom, J.L. Ruth, and P. Warwick J. Org. Chem. 46 1981 1432 1441
189. S. Ma, and Z. Yu J. Org. Chem. 68 2003 6149 6152
190. S.R. Foley, H. Shen, U.A. Qadeer, and R.F. Jordan Organometallics 23 2004 600 609
191. B. Alcaide, P. Almendros, J.M. Alonso, M.T. Quirós, and P. Gadziński Adv. Synth. Catal. 353 2011 1871 1876
192. F.L. Yang, X.T. Ma, and S.K. Tian Chem. - Eur. J. 18 2012 1582 1585
193. Y. Zhang, K.A. DeKorver, A.G. Lohse, Y.-S. Zhang, J. Huang, and R.P. Hsung Org. Lett. 11 2009 899 902
194. M.-B. Li, Y. Wang, and S.-K. Tian Angew. Chem., Int. Ed. 51 2012 2968 2971 or from isomerisation reactions
195. B. Ferber, S. Lemaire, M.M. Mader, G. Prestat, and G. Poli Tetrahedron Lett. 44 2003 4213 4216
196. T. Oshitari, R. Akagi, and T. Mandai Synthesis 2004 1325 1330
197. V.I. Timokhin, N.R. Anastasi, and S.S. Stahl J. Am. Chem. Soc. 125 2003 12996 12997
198. In the absence of an effective Bronstedt base, the aminopalladation can be a reversible process: V.I. Timokhin, and S.S. Stahl J. Am. Chem. Soc. 127 2005 17888 17893
199. R. Tamura, A. Kamimura, and N. Ono Synthesis 1991 423 434
200. A. Barco, S. Benetti, G. Spalluto, A. Casolari, G.P. Pollini, and V. Zanirato J. Org. Chem. 57 1992 6279 6286
201. T. Nakano, M. Miyahara, T. Itoh, and A. Kamimura Eur. J. Org. Chem. 2012 2161 2166
202. G.T. Crisp, and P.T. Glink Tetrahedron 48 1992 3541 3556
203. S. Cacchi, G. Fabrizi, A. Goggiamani, and A. Sferrazza Org. Biomol. Chem. 9 2011 1727 1730
204. L.-C. Kao, F.G. Stakem, B.A. Patel, and R.F. Heck J. Org. Chem. 47 1982 1267 1277
205. N.J. Malek, and A.E. Moormann J. Org. Chem. 47 1982 5395 5397
206. A. Arcadi, E. Bernocchi, S. Cacchi, L. Caglioti, and F. Marinelli Tetrahedron Lett. 31 1990 2463 2466
207. G.T. Crisp, and M.G. Gebauer Tetrahedron 52 1996 12465 12474
208. C.A. Busacca, and Y. Dong Tetrahedron Lett. 37 1996 3947 3950
209. Y. Dong, and C.A. Busacca J. Org. Chem. 62 1997 6464 6465
210. P. Prediger, L.F. Barbosa, Y. Génisson, and C.R.D. Correia J. Org. Chem. 76 2011 7737 7749
211. Y. Deng, Z. Jiang, M. Yao, D. Xu, L. Zhang, H. Li, W. Tang, and L. Xu Adv. Synth. Catal. 354 2012 899 907
212. A.R. Kore, and M. Shanmugasundaram Tetrahedron Lett. 53 2012 2530 2532
213. Z. Jiang, L. Zhang, C. Dong, B. Ma, W. Tang, L. Xu, Q. Fan, and J. Xiao Tetrahedron 68 2012 4919 4926
214. Z. Lu, and S.S. Stahl Org. Lett. 14 2012 1234 1237
215. S.R. Fix, J.L. Brice, and S.S. Stahl Angew. Chem., Int. Ed. 41 2002 164 166
216. V. Kotov, C.C. Scarborough, and S.S. Stahl Inorg. Chem. 46 2007 1910 1923
217. X. Ye, G. Liu, B.V. Popp, and S.S. Stahl J. Org. Chem. 76 2011 1031 1044
218. J.E. Redford, R.I. McDonald, M.L. Rigsby, J.D. Wiensch, and S.S. Stahl Org. Lett. 14 2012 1242 1245
219. K.J. Fraunhoffer, and M.C. White J. Am. Chem. Soc. 129 2007 7274 7276
220. C. Jiang, D.J. Covell, A.F. Stepan, M.S. Plummer, and M.C. White Org. Lett. 14 2012 1386 1389
221. D.D. Keith, J.A. Tortora, K. Ineichen, and W. Leimgruber Tetrahedron 31 1975 2633 2636
222. L. Filippini, M. Gusmeroli, and R. Riva Tetrahedron Lett. 34 1993 1643 1646
223. M.M. Rogers, V. Kotov, J. Chatwichien, and S.S. Stahl Org. Lett. 9 2007 4331 4334
224. J.L. Brice, J.E. Harang, V.I. Timokhin, N.R. Anastasi, and S.S. Stahl J. Am. Chem. Soc. 127 2005 2868 2869
225. 3- allylpalladium intermediates, i.e., Tsuji-Trost type reactions, rather than aza-Wacker reactions followed by β′-H eliminations: G. Liu, G. Yin, and L. Wu Angew. Chem., Int. Ed. 47 2008 4733 4736
226. B. Åkermark, J.E. Bäckvall, K. Siirala-Hanseń, K. Sjöberg, and K. Zetterberg Tetrahedron Lett. 15 1974 1363 1366
227. B. Åkermark, J.E. Bäckvall, L.S. Hegedus, K. Zetterberg, K. Siirala-Hansén, and K. Sjöberg J. Organomet. Chem. 72 1974 127 138
228. P. Lv, K. Huang, L. Xie, and X. Xu Org. Biomol. Chem. 9 2011 3133 3135
229. A. Hallberg, and C. Westerlund Chem. Lett. 1982 1993 1994
230. K. Kikukawa, K. Ikenaga, F. Wada, and T. Matsuda Chem. Lett. 1983 1337 1340
231. K. Kikukawa, K. Ikenaga, K. Kono, K. Toritani, F. Wada, and T. Matsuda J. Organomet. Chem. 270 1984 277 282
232. K. Ikenaga, S. Matsumoto, K. Kikukawa, and T. Matsuda Chem. Lett. 1988 873 876
233. Another possibility would be a transmetalation promoted by fluoride ion: Y. Hatanaka, and T. Hiyama Synlett 1991 845 853 The transmetalation process occurs from alkenylpentafluorosilicates (Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, R.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542-549.), alkenylsilanoates (Denmark, S. E.; Regens, C. S. Acc. Chem. Res. 2008, 41, 1486-1499.) and intramolecularly activated vinylsilanes (Matsumoto, K.; Shindo, M. Adv. Synth. Catal. 2012, 354, 642-650. Omote, M.; Tanaka, M.; Ikeda, A.; Nomura, S.; Tarui, A.; Sato, K.; Ando, A. Org. Lett. 2012, 14, 2286-2289.).
234. K. Ikenaga, K. Kikukawa, and T. Matsuda J. Chem. Soc., Perkin Trans. 1 1986 1959 1964
235. D. Alvisi, E. Blart, B.F. Bonini, G. Mazzanti, A. Ricci, and P. Zani J. Org. Chem. 61 1996 7139 7146
236. K. Karabelas, and A. Hallberg J. Org. Chem. 51 1986 5286 5290
237. K. Kikukawa, K. Ikenaga, F. Wada, and T. Matsuda Tetrahedron Lett. 25 1984 5789 5792
238. K. Ikenaga, K. Kikukawa, and T. Matsuda J. Org. Chem. 52 1987 1276 1280
239. K. Karabelas, and A. Hallberg Tetrahedron Lett. 26 1985 3131 3132
240. K. Karabelas, and A. Hallberg J. Org. Chem. 53 1988 4909 4914
241. For other efficient conditions with ArI, which preserve the trimethylsilyl group, see: T. Jeffery Tetrahedron Lett. 40 1999 1673 1676
242. Y. Hatanaka, Y. Ebina, and T. Hiyama J. Am. Chem. Soc. 113 1991 7075 7076
243. Y. Hatanaka, K. Goda, and T. Hiyama Tetrahedron Lett. 35 1994 1279 1282
244. Y. Hatanaka, K. Goda, and T. Hiyama Tetrahedron Lett. 35 1994 6511 6514
245. K. Karabelas, C. Westerlund, and A. Hallberg J. Org. Chem. 50 1985 3896 3900
246. L.F. Tietze, and R. Schimpf Angew. Chem., Int. Ed. Engl. 33 1994 1089 1091
247. 4 (Ref. 190. L.F. Tietze, and T. Raschke Synlett 1995 597 598
248. L.F. Tietze, and T. Raschke Liebigs Ann./Recueil 1996 1981 1987) are, in our opinion, surprising. This leads us to suspect other intermediates than those of the Heck-type reaction, possibly η3-allylpalladium complexes.
249. II salts has been reported: J.M. Kliegman J. Organomet. Chem. 29 1971 73 77
250. R.J.P. Corriu, N. Escudié, and C. Guérin J. Organomet. Chem. 271 1984 C7 C9
251. T. Hayashi, M. Konishi, Y. Okamoto, K. Kabeta, and M.J. Kumada Org. Chem. 51 1986 3772 3781
252. K. Fugami, K. Oshima, K. Utimoto, and H. Nozaki Bull. Chem. Soc. Jpn. 60 1987 2509 2515
253. For corresponding catalytic reactions, see: J. Muzart, and A. Riahi Organometallics 11 1992 3478-3481
254. I. Macsári, and K.J. Szabó Chem. - Eur. J. 7 2001 4097 4106 These reactions involve transmetalation reactions
255. T. Jeffery Tetrahedron Lett. 41 2000 8445 8449
256. J.R. McAtee, S.E.S. Martin, D.T. Ahneman, K.A. Johnson, and D.A. Watson Angew. Chem., Int. Ed. 51 2012 3663 3667
257. J. Muzart J. Mol. Catal. A: Chem. 319 2010 1 29
258. II under these reaction conditions: J. Muzart Tetrahedron 63 2007 7505 7521
259. S. Igarashi, Y. Haruta, M. Ozawa, Y. Nishide, H. Kinoshita, and K. Inomata Chem. Lett. 1989 737 740
260. Y. Hattori, S. Furuhata, M. Okajima, H. Konno, M. Abe, H. Miyoshi, T. Goto, and H.A. Makabe Org. Lett. 10 2008 717 720
261. S. Furuhata, Y. Hattori, M. Okajima, H. Konno, M. Abe, H. Miyoshi, T. Goto, and H.A. Makabe Tetrahedron 64 2008 7695 7703
262. J. Uenishi, and Y.S. Vikhe Heterocycles 80 2010 1463 1469
263. O. Roy, A. Riahi, F. Hénin, and J. Muzart Tetrahedron 56 2000 8133 8140
264. J.S. Cannon, A.C. Olson, L.E. Overman, and N.S. Solomon J. Org. Chem. 77 2012 1961 1973
265. E. Bayer, and K. Geckeler Angew. Chem., Int. Ed. Engl. 18 1979 533 534
266. J. Xu, Y. Fu, B. Xiao, T. Gong, and Q. Guo Tetrahedron Lett. 51 2010 5476 5479
267. J.L. Brice, J.E. Meerdink, and S.S. Stahl Org. Lett. 6 2004 1845 1848
268. J. Muzart Eur. J. Org. Chem. 2007 3077 3089
269. J. Eustache, P. Van de Weghe, D. Le Nouen, H. Uyehara, C. Kabuto, and Y. Yamamoto J. Org. Chem. 70 2005 4043 4053
270. H. Yokoyama, H. Ejiri, M. Miyazawa, S. Yamaguchi, and Y. Hirai Tetrahedron: Asymmetry 18 2007 852 856
271. H. Yokoyama, H. Kobayashi, M. Miyazawa, S. Yamaguchi, and Y. Hirai Heterocycles 74 2007 283 292
272. H. Yokoyama, and Y. Hirai Heterocycles 75 2008 2133 2153
273. H. Yokoyama, Y. Hayashi, Y. Nagasawa, H. Ejiri, M. Miyazawa, and Y. Hirai Tetrahedron 66 2010 8458 8463
274. S. Saito, T. Hara, N. Takahashi, M. Hirai, and T. Morikawe Synlett 1992 237 238
275. M. Kimura, H. Harayama, S. Tanaka, and Y. Tamaru J. Chem. Soc., Chem. Commun. 1994 2531 2533
276. Y. Hirai, J. Watanabe, T. Nozaki, H. Yokoyama, and S. Yamaguchi J. Org. Chem. 62 1997 776 777
277. A. Lei, G. Liu, and X. Lu J. Org. Chem. 67 2002 974 980
278. B. Ferber, G. Prestat, S. Vogel, D. Madec, and G. Poli Synlett 2006 2133 2135
279. J.S. Cannon, S.F. Kirsch, and L.E. Overman J. Am. Chem. Soc. 132 2010 15185 15191
280. S.F. Kirsch, and L.E. Overman J. Am. Chem. Soc. 127 2005 2866 2867
281. J.S. Cannon, J.H. Frederich, and L.E. Overman J. Org. Chem. 77 2012 1939 1951
282. S.F. Kirsch, L.E. Overman, and N.S. White Org. Lett. 9 2007 911 913
283. A.C. Olson, L.E. Overman, H.F. Sneddon, and J.W. Ziller Adv. Synth. Catal. 351 2009 3186 3192
284. J.S. Cannon, S.F. Kirsch, L.E. Overman, and H.F. Sneddon J. Am. Chem. Soc. 132 2010 15192 15203
285. A.G. Steinig, and A. de Meijere Eur. J. Org. Chem. 1999 1333 1334
286. H.M. Guo, W.H. Rao, H.Y. Niu, L.L. Jiang, L. Liang, Y. Zhang, and G.R. Qu RSC Adv. 1 2011 961 963
287. R.F. Heck J. Am. Chem. Soc. 93 1971 6896 6901
288. H.A. Dieck, and R.F. Heck J. Am. Chem. Soc. 96 1974 1133 1136
289. H.A. Carless, and D.J. Haywood J. Chem. Soc., Chem. Commun. 1980 980 981
290. Y. Hoshino, and N. Takeno Bull. Chem. Soc. Jpn. 67 1994 2873 2875
291. Y.Q. Zhang, D.Y. Zhu, B.S. Li, Y.Q. Tu, J.X. Liu, Y. Lu, and S.H. Wang J. Org. Chem. 77 2012 4167 4170
292. K. Takeda, and M. Toyota Heterocycles 84 2012 1271 1276
293. L.F. Tietze, T. Nöbel, and M. Spescha J. Am. Chem. Soc. 120 1998 8971 8977
294. M. Gowan, A.S. Caillé, and C.K. Lau Synlett 1997 1312 1314
295. P. Zakrzewski, M. Gowan, L.A. Trimble, and C.K. Lau Synthesis 1999 1893 1902
296. I. Pefiel, I.M. Pastor, and M. Yus Eur. J. Org. Chem. 2012 3151 3156
297. C.R.D. Correia, C.C. Oliveira, A.G. Salles, and E.A.F. Santos Tetrahedron Lett. 53 2012 3325 3328
298. N.G. Andersen, M. Parvez, and B.A. Keay Org. Lett. 2 2000 2817 2820
299. N.G. Andersen, M. Parvez, R. McDonald, and B.A. Keay Can. J. Chem. 82 2004 145 161
300. D.St.C. Black, P.A. Keller, and N. Kumar Tetrahedron 48 1992 7601 7608
301. E.W. Werner, and M.S. Sigman J. Am. Chem. Soc. 132 2010 13981 13983
302. M.S. Sigman, and E.W. Werner Acc. Chem. Res. 45 2012 874 884
303. P. Pinho, J. Minnaard, and B.L. Feringa Org. Lett. 5 2003 259 261
304. S. Merten, R. Froehlich, O. Kataeva, and P. Metz Adv. Synth. Catal. 347 2005 754 758