Contribution of electrochemistry to organometallic catalysis

Chemical Reviews

Volumn 108, Issue 7, 2008, Pages 2300-2347

  Jutand, Anny ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMISTRY; ELECTROCHEMISTRY; ELECTROLYSIS; MECHANISMS; ORGANOMETALLICS; TRANSITION METALS;

CATALYTIC CYCLING; CATALYTIC REACTIONS; CATALYZED REACTIONS; CHEMICAL REDUCTIONS; ELECTROCHEMICAL TECHNIQUES; ELECTRON TRANSFER; IN-SITU; ORGANOMETALLIC CATALYSIS;

METALS;

EID: 49149125488     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr068072h     Document Type: Article

References (247)

1. Principles and Applications of Organotransition Metal Chemistry; Collman, J. P., Hegedus, L. S., Norton, J. R., Finke, R. G., Eds.; Oxford University Press: Mill Valley, CA, 1987.
2. Comprehensive Organometallic Chemistry III, Crabtree, R., Mingos, M., Eds.; Elsevier: Amsterdam, 2006, Vols 1-13.
3. Amatore, C.; Jutand, A. J. Organomet. Chem. 1999, 576, 254.
4. Kozuch, S.; Amatore, C.; Jutand, A.; Shaik, S. Organometallics 2005, 24, 2319.
5. Faulkner, L. R. J. Chem. Educ. 1983, 60, 262.
6. Bard, A. J.; Faulkner, L. R. Electrochemical Methods. Fundamentals and Applications, 2nd ed.; Wiley: New York, 2001.
7. Savéant, J.-M. Elements of Molecular and Biomolecular Electrochemistry. An Electrochemical Approach to Electron Transfer Chemistry; Wiley: Hoboken, NJ, 2006.
8. Amatore, C. In Electrochemistry at Ultramicroelectrodes in Physical Electrochemistry; Rubinstein, I., Ed.; Marcel Dekker, New York, 1995; Chapter 4.
9. Atkins, P. W. Physical Chemistry, 5th ed.; University Press: 1994.
10. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley-Interscience, New York, 2002, Vols. I and II I].
11. For the history of Pd-catalyzed reactions, see: Tsuji, J. New J. Chem. 2000, 24, 127.
12. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Soc. Chim. Jpn. 1971, 44, 581.
13. Heck, R. F.; Nolley, J. P., Jr J. Org. Chem. 1972, 37, 2320.
14. Cassar, L. J. Organomet. Chem. 1975, 93, 253.
15. Dieck, H. A.; Heck, R. F. J. Organomet. Chem. 1975, 93, 259.
16. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 50, 4467.
17. Fauvarque, J.-F.; Jutand, A. Bull. Soc. Chim. 1976, 765.
18. Negishi, E.-i.; King, A. 0.; Okukado, N. J. Org. Chem. 1977, 42, 1921.
19. Fauvarque, J.-F.; Jutand, A. J, Organomet. Chem. 1977, 132, C17.
20. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992.
21. Miyaura, N.; Suzuki, A. J. Chem. Soc., Chem. Commun. 1979, 19, 866.
22. Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1988, 29, 97.
23. Fitton, P.: Johnson, M. P.; McKeon, J. E. J. Chem. Soc., Chem. Commun. 1968, 6.
24. Fitton, P.; Rick, E. A. J. Organomet. Chem. 1971, 28, 287.
25. Mann, B. E.; Musco, A. J. Chem. Soc., Dalton Trans. 1975, 1673.
26. Fauvarque, J. F.; Pflüger, F.; Troupel, M. J. Organomet. Chem. 1981, 208, 419.
27. Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; L.; Mottier, L Organometallics 1993, 12, 3168.
28. Amatore, C.; Pflüger, F. Organometallics 1990, 9, 2276.
29. Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319.
30. Jutand, A.; Mosleh, A Organometallics 1995, 14, 1810.
31. Ritter, K. Synthesis 1993, 735.
32. Sakamoto, T.; Kondo, Y.; Mutura, N.; Yamanaka, H. Tetrahedron 1993, 49, 9713.
33. Kakino, R.; Yasumi, S.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 137.
34. Jutand, A.; Negri, S.; de Vries, J. G. Eur. J. Inorg. Chem. 2002, 1711.
35. Amatore, C.; Godin, B.; Jutand, A.; Ferber, B.; Top, S.; Jaouen, G. Organometallics 2007, 23, 3887.
36. Yamamura, M.; Moritani, S. I.; Murahashi, J. J. Organomet. Chem. 1975, 91, C39.
37. Fauvarque, J.-F.; Jutand, A J. Organomet. Chem. 1981, 209, 109.
38. Jutand, A.; Negri, S. Organometallics 2003, 22, 422.
39. Amatore, C.; Jutand, A. Coord. Chem. Rev. 1998, 178-180, 511.
40. Amatore, C.; Jutand, A.; Meyer, G. Inorg. Chim. Acta 1998, 273, 76.
41. Amatore, C.; Jutand, A.; Meyer, G.; Atmani, H.; Khalil, F.; Ouazzani Chahdi, F. Organometallics 1998, 17, 2958.
42. Amatore, C.; Jutand, A.; Thuilliez, A. J. Organomet. Chem. 2002, 643-644, 416.
43. Amatore, C.; Bucaille, A.; Fuxa, A.; Jutand, A.; Meyer, G.; Ndedi Ntepe, A. Chem.-Eur. J. 2001, 7, 2134.
44. Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162.
45. Amatore, C.; Broeker, G.; Jutand, A.; Khalil, F. J. Am. Chem. Soc. 1997, 119, 5176.
46. Paladino, G.; Madec, D.; Prestat, G.; Maitro, G.; Poli, G.; Jutand, A Organometallics 2007, 26, 455.
47. Amatore, C.; Fuxa, A.; Jutand, A. Chem.-Eur. J. 2000, 6, 1474.
48. Macé, Y.; Kapdi, A. R.; Fairlamb, I. J. S.; Jutand, A. Organometallics 2006, 25, 1795.
49. Amatore, C.; Carré, C.; Jutand, A.; Medjour, Y. Organometallics 2002, 21, 4540.
50. Amatore, C.; Bensalem. S.; Ghalem, S.; Jutand, A.; Medjour, Y. Eur. J. Org. Chem. 2004, 366.
51. Jutand, A. Pure Appl. Chem. 2004, 76, 565.
52. Yoshida, T.; Otsuka, S. Inorg. Synth. 1990, 28, 113.
53. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 4, 3030.
54. Galardon, E.; Ramdeehul, S.; Brown, J. M.; Cowley, A.; Hii, K. K.; Jutand, A. Angew. Chem., Int. Ed. 2002, 41, 1760.
55. Kurbangalieva, A.; Hii, K. K.; Galardon, E.; Carmichael, D.; Brown, J. M.; Jutand, A. Manuscript in preparation.
56. Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373.
57. Amatore, C.; Azzabi, M.; Jutand, A. J. Organomet. Chem. 1989, 363, C41.
58. Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375.
59. Amatore, C.; Azzabi, M.; Calas, P.; Jutand, A.; Lefrou, C.; Rollin, Y. J. Electroanal. Chem. 1990, 288, 45.
60. Kozuch, S.; Shaik, S.; Jutand, A.; Amatore, C. Chem.-Eur. J. 2004, 10, 3072.
61. Negishi, E.-i.; Takahashi, T.; Akiyoshi, K J. Chem. Soc., Chem. Commun. 1986, 1338.
62. Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
63. Negishi, E.-i Bull. Soc. Chim. Jpn 2007, 80, 233.
64. Herrmann, W. A.; Elison, M.; Fischer, J.; Köcher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2371.
65. Cloke, F. G. N.; Geldbach, T.; Hitchcock, P. B. Organometallics 1999, 18, 3228.
66. Titcomb, L. R.; Caddick, S.; Clocke, F. G. N.; Wilson, D. J.; McKerrecher, D. Chem. Commun. 2001, 1388.
67. Guinness, D. S.; Cavell, K. J.; Skelton, B. W.; White, A. H. Organometallics 1999, 18, 1596.
68. Caddick, S.; Cloke, F. G. N.; Hitchcock, P. B.; Leonard, J.; Lewis, A. K. K.; McKerrecher, D.; Titcomb, L. R. Organometallics 2002, 21, 4318.
69. Lewis, A. K. K.; Caddick, S.; Cloke, F. G. N.; Billingham, N. C.; Hitchcock, P. B.; Leonard, J. J. Am. Chem. Soc. 2003, 125, 10066.
70. Pytkowicz, J.; Roland, S.; Mangeney, P.; Meyer, G.; Jutand, A. J. Organomet. Chem. 2003, 678, 166.
71. Roland, S.; Mangeney, P.; Jutand, A. Synlett 2006, 3088.
72. Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133.
73. Heck, R. F. Org. React. 1982, 27, 345.
74. Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009.
75. Osawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177.
76. Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G Organometallics 1995, 14, 1818.
77. Amatore, C.; Jutand, A.; Lemaître, F.; Ricard, J. L.; Kozuch, S.; Shaik, S. J. Organomet. Chem. 2004, 689, 3728.
78. Amatore, C.; Jutand, A.; Medeiros, M. J. New J. Chem. 1996, 20, 1143.
79. Amatore, C.; Blart, E.; Genêt, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829.
80. Gélin, E.; Amengual, R.; Michelet, V.; Savignac, M.; Jutand, A.; Genêt, J. P. Adv. Synth. Catal. 2004, 346, 1733.
81. Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605.
82. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
83. Amatore, C.; Jutand, A.; Thuilliez, A. Organometallics 2001, 20, 3241.
84. Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. 1995, 34, 1844.
85. Herrmann, W. A.; Böhm, V. P. W.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23.
86. Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. 1996, 35, 2359.
87. Sundermann, A.; Uzan, O.; Martin, J. M. L. Chem. - Eur. J. 2001, 7, 1703.
88. Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29.
89. Böhm, V. P. W.; Herrmann, W. A. Chem. - Eur. J. 2001, 7, 4191.
90. d'Orlyé, F.; Jutand, A. Tetrahedron 2005, 61, 9670.
91. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
92. Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ndedi Ntepe, A.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212.
93. Amatore, C.; Carré, C.; Jutand, A. Acta Chem. Scand. 1998, 52, 100.
94. For a review on the characterization of coordination compounds by conductivity measurements, see: Geary, W. J. Coord. Chem. Rew. 1971, 7, 81.
95. Jutand, A.; Mosleh, A. J. Org. Chem. 1997, 62, 261.
96. Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
97. Hii, K. K.; Thornton-Pett, M.; Jutand, A.; Tooze, R. P Organometallics 1999, 18, 1887.
98. Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. Acc. Chem. Res. 1990, 23, 34.
99. Zargarian, D.; Alper, H. Organometallics 1993, 12, 712.
100. Carelli, I.; Chiarotto, I.; Cacchi, S.; Pace, P.; Amatore, C.; Jutand, A.; Meyer, G. Eur. J. Org. Chem. 1999, 1471.
101. For a review on hydrido complexes of palladium, see: Grushin, V. V Chem. Rev. 1996, 96, 2011.
102. Trost, B. M. Chem. - Eur. J. 1998, 4, 2405.
103. Amatore, C.; Jutand, A.; Meyer, G.; Carelli, I.; Chiarotto, I. Eur. J. Inorg. Chem. 2000, 1855.
104. Tsuji, J. Palladium Reagents and catalysts; John Wiley & Sons: Chichester, U.K., 1996, p 290.
105. Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
106. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. F.; McElvain, S. M. Tetrahedron Lett. 1979, 25, 2301.
107. 2 with monodentate phosphines in allylic substitutions, see: Ferroud, D.; Genêt, J. P.; Muzart, J. Tetrahedron Lett. 1984, 25, 4379.
108. 2 with bidentate phosphines in allylic substitutions, see: Fiaud, J.-C.; Hibon de Gournay, A.; Larchevêque, M. J. Organomet. Chem. 1978, 154, 175.
109. Amatore, C.; Jutand, A.; Meyer, G.; Mottier, L. Chem. - Eur. J. 1999, 5, 466.
110. Amatore, C.; Gamez, S.; Jutand, A. Chem. - Eur. J. 2001, 7, 1273.
111. Amatore, C.; Gamez, S.; Jutand, A.; Meyer, G.; Mottier, L. Electrochim. Acta 2001, 46, 3237.
112. Agenet, N.; Amatore, C.; Gamez, S.; Gérardin, H.; Jutand, A.; Meyer, G.; Orthwein, C ARKIVOC 2002, 92; http:/ /www.arkat-usa.org/
113. Amatore, C.; Jutand, A.; Mensah, L.; Fiaud, J.-C.; Legros, J.-Y. Eur. J. Org. Chem. 2006, 1185.
114. Bäckvall, J.-E.; Granberg, K. L.; Heumann, A. Isr. J. Chem. 1991, 31, 17.
115. Granberg, K. L.; Bäckvall, J.-E J. Am. Chem. Soc. 1992, 114, 6858.
116. Tsuji, J. Tetrahedron 1986, 42, 4361.
117. Amatore, C.; Gamez, S.; Jutand, A.; Meyer, G.; Moreno-Mañas, M.; Morral, L.; Pleixats, R Chem. - Eur. J. 2000, 6, 3372.
118. Moreno-Mañas, M.; Morral, L.; Pleixats, R. J. Org. Chem. 1998, 63, 6160.
119. Jutand, A. Eur. J. Inorg. Chem. 2003, 2017.
120. Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421.
121. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
122. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
123. Farina, V. Adv. Synth. Catal. 2004, 346, 1553.
124. Amatore, C.; Godin, G.; Jutand, A.; Lemaitre, F. Chem.-Eur. J. 2007, 13, 2002.
125. Amatore, C.; Godin, G.; Jutand, A.; Lemaitre, F. Organometallics 2007, 26, 1757.
126. Mo, J.; Xu, L.; Xiao, J. J. Am. Chem. Soc. 2005, 127, 751.
127. Farina, V.; Roth, G. P., Recent Advances in the Stille Reaction in Advances in Metal-Organic Chemistry; JAI Press Inc.: 1996, Vol, 1.
128. Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction in Organic Reactions, Wiley: New York, 1997; Vol 50, p 1.
129. Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978.
130. Alvarez, R.; Faza, O. N.; Lopez, C. S.; de Lera, A. R. Org. Lett. 2006, 35.
131. Nova, A.; Ujaque, G.; Maseras, F.; Lledos, A.; Espinet, P. J. Am. Chem. Soc. 2006, 128, 14571.
132. Tougerti, A.; Negri, S.; Jutand, A. Chem.-Eur. J. 2007, 13, 666.
133. Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403.
134. Jutand, A.; Negri, S.; Principaud, A. Eur. J. Inorg. Chem. 2005, 631.
135. Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
136. For dppp as figand, see: Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2003, 44, 1541.
137. Miyaura, N. Advances in Metal-Organic Synthesis; JAI Press Inc.: 1998, Vol 6, p 187.
138. Adamo, C.; Amatore, C.; Ciofini, I.; Jutand, A.; Lakmini, H. J. Am. Chem. Soc. 2006, 128, 6829.
139. Moreau, X.; Campagne, J. M. J. Organomet. Chem. 2003, 687, 322.
140. For the seminal use of dppf ligand in C-S coupling, see: Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1995, 36, 4133.
141. Moreau, X; Campagne, J. M.; Meyer, G.; Jutand, A. Eur. J. Org. Chem. 2005, 3749.
142. Lund, H. In Organic Electrochemistry, 4th ed.; Lund, H., Hammerich, O., Eds.; Marcel Dekker Inc: New York, 2001.
143. Organic Electrochemistry; Schäfer, H. J., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
144. Torii, S. Synthesis 1986, 873.
145. Steckhan, E. Angew. Chem., Int. Ed. Engl. 1986, 25, 683.
146. Chaussard, J.; Folest, J.-C.; Nédélec, J.-Y.; Périchon, J.; Troupel, M. Synthesis 1990, 5, 369.
147. Nédélec, J.-Y.; Périchon, J.; Troupel, M. Top. Curr. Chem. ] 1997, 18, 5-141.
148. Duñach, E.; Franco, D.; Olivero, S. Eur. J. Org. Chem. 2003, 1605.
149. Sock, O.; Troupel, M.; Périchon, J. Tetrahedron Lett. 1985, 26, 1509.
150. Troupel, M.; Rollin, Y.; Périchon, J.; Fauvarque, J.-F. Nouv. J. Chim. 1981, 5, 621.
151. Fauvarque, J.-F.; Chevrot, C.; Jutand, A.; François, M.; Périchon, J. J. Organomet. Chem. 1984, 264, 273.
152. Amatore, C.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 2819.
153. Amatore, C.; Jutand, A. J. Electroanal. Chem. 1991, 306, 141.
154. Fauvarque, J.-F.; Jutand, A.; François, M.; Petit, M. A. J. Appl. Electrochem. 1988, 18, 116.
155. Fauvarque, J.-F.; Jutand, A.; François, M. Nouv. J. Chim. 1986, 10, 119.
156. Fauvarque, J.-F.; Jutand, A.; François, M. J. Appl. Electrochem. 1998, 18, 109.
157. Fauvarque, J.-F.; De Zélicourt, Y.; Amatore, C.; Jutand, A. J. Appl. Electrochem. 1990, 20, 338.
158. Fauvarque, J.-F.; De Zélicourt, Y.; Amatore, C.; Jutand, A., Compagnie Générale d'Electricité, CGE SA,French Patent 86/0571, 1986.
159. Amatore, C.; Jutand, A. Organometallics 1988, 7, 2203.
160. Amatore, C.; Jutand, A.; Mottier, L. J. Electroanal. Chem. 1991, 306, 125.
161. Amatore, C.; Jutand, A. Acta Chem. Scand. 1990, 44, 755.
162. Rollin, Y.; Troupel, M.; Tuck, D. G.; Périchon, J. J. Organomet. Chem. 1986, 303, 131.
163. Meyer, G.; Troupel, M.; Périchon, J. J. Organomet. Chem. 1990, 393, 137.
164. Courtois, V.; Barhdadi, R.; Troupe], M.; Périchon, J. Tetrahedron 1997, 53, 11569.
165. Raynal, F.; Barhdadi, R.; Périchon, J.; Savall, A.; Troupel, M. Adv. Synth. Catal. 2002, 344, 45.
166. Barhdadi, R.; Courtinard, C.; Nédélec, J.-Y.; Troupel, M. Chem. Commun. 2003, 1434.
167. Mellah, M.; Gmouh, S.; Vaultier, M.; Jouikov, V. Electrochem. Commun. 2003, 5, 591.
168. de França, K. W. R.; Navarro, M.; Léonel, E.; Durandetti, M.; Nédélec, J.-Y. J. Org. Chem. 2002, 67, 1838.
169. de França, K. W. R.; de Lira Oliviera, J.; Florêncio, T.; da Silva, A. P.; Navarro, M.; Léonel, E.; Nédélec, J.-Y. J. Org. Chem. 2005, 70, 10778.
170. Durandetti, M.; Devaud, M.; Périchon, J. New J. Chem. 1996, 20, 659.
171. Courtois, V.; Barhdadi, R.; Condon, S.; Troupel, M. Tetrahedron Lett. 1999, 40, 5993,
172. Cannes, C.; Labbé, E.; Durandetti, M.; Devaud, M.; Périchon, J. J. Electroanal. Chem. 1996, 412, 85.
173. Cannes, C.; Condon, S.; Durandetti, M.; Périchon, J.; Nédélec, J.-Y. J. Org. Chem. 2000, 65, 4575.
174. Fauvarque, J.-F.; Petit, M. A.; Pflüger, F.; Jutand, A.; Chevrot, C.; Troupel, M. Makromol. Chem. 1983, 4, 455.
175. Fauvarque, J.-F.; Digua, A.; Petit, M. A.; Savard, J. Makromol. Chem. 1985, 186, 2415.
176. Aboukassim, A.; Chevrot, C. Polymer 1993, 34, 401.
177. Mellah, M.; Labbé, E.; Nédélec, J.-Y.; Périchon, J. New J. Chem. 2002, 26, 207.
178. Zotti, G.; Schiavon, G.; Comisso, N.; Berlin, A.; Pagani, G. Synth. Met. 1990, 36, 337.
179. Utley, J. H. P.; Gao, Y.; Gruber, J.; Lines, R. J. Mater. Chem. 1995, 5, 1297.
180. Amatore, C.; Gaubert, F.; Jutand, A.; Utley, J. H. P. J. Chem. Soc., Perkin Trans. 1996, 2, 2447.
181. Kijima, M.; Sakai, Y.; Shirakawa, H. Chem. Lett. 1994, 2011.
182. Conan, A.; Sibille, S.; d'Incan, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1990, 48.
183. Durandetti, M.; Sibille, S.; Nédélec, J.-Y.; Périchon, J. Synth. Commun. 1994, 24, 145.
184. Durandetti, M.; Nédélec, J.-Y.; Périchon, J. J. Org. Chem. 1996, 61, 1748.
185. Durandetti, M.; Périchon, J.; Nédélec, J.-Y. Tetrahedron Lett. 1997, 38, 8683.
186. Durandetti, M.; Périchon, J.; Nédélec, J.-Y. J. Org. Chem. 1997, 62, 7914.
187. Gomes, P.; Gosmini, C.; Péricbon, J. Tetrahedron 2003, 59, 2999.
188. Buriez, O.; Nédélec, J.-Y.; Périchon, J. J. Electroanal. Chem. 2001, 506, 162.
189. Polleux, L.; Labbé, E.; Buriez, O.; Périchon, J. Chem.-Eur. J. 2005, 11, 4678.
190. Gomes, P.; Gosmini, C.; Périchon, J. J. Org. Chem. 2003, 68, 1142.
191. Gomes, P.; Buriez, O.; Labbé, E.; Gosmini, C.; Périchon, J. J. Electroanal. Chem. 2004, 562, 255.
192. Scheffold, R.; Dike, M.; Dike, S.; Herold, T.; Walder, L. J. Am Chem. Soc. 1980, 102, 3642.
193. Scheffold, R.; Abrecht, S.; Orfinski, R.; Ruf, H.-R.; Stamouli, P.; Tinembart, O.; Walder, L.; Weymuth, C. Pure Appl. Chem. 1987, 59, 363.
194. Torii, S.; Tanaka, H.; Hamatani, T.; Morisaki, K.; Jutand, A.; Pflüger, F.; Fauvarque, J.-F. Chem. Lett. 1986, 169.
195. Amatore, C.; Jutand, A.; Khalil, F.; Nielsen, M. F. J. Am. Chem. Soc. 1992, 114, 7076.
196. Jutand, A.; Négri, S. Eur. J. Org. Chem. 1998, 1811.
197. Jutand, A.; Négri, S.; Mosleh, A. J. Chem. Soc., Chem. Commun. 1992, 1729.
198. Jutand, A.; Négri, S. Synlett 1997, 719.
199. Kamekawa, H.; Senboku, H.; Tokuda, M. Tetrahedron Lett. 1998, 39, 1591.
200. Senboku, H.; Fujimura, Y.; Kamekawa, H.; Tokuda, M. Electrochim. Acta 2000, 45, 2995.
201. Kamekawa, H.; Senboku, H.; Tokuda, M. Electrochim. Acta 1997, 42, 2117.
202. Kamekawa, H.; Kudoh, H.; Senboku, H.; Tokuda, M. Chem. Lett. 1997, 917.
203. Torii, S.; Tanaka, H.; Morisaki, K. Tetrahedron Lett. 1985, 26, 1655.
204. Amatore, C.; Carré, E.; Jutand, A.; Tanaka, H.; Ren, Q.; Torii, S. Chem.-Eur. J. 1996 2, 1729.
205. Marzouk, H.; Rollin, Y.; Folest, J. C.; Nédélec, J.-Y.; Périchon, J. J. Organomet. Chem. 1989, 369, C47.
206. Amatore, C.; Jutand, A.; Périchon, J.; Rollin, Y. Monatsh. Chem. 2000, 131, 1293.
207. Sengmany, S.; Léonel, E.; Paugam, J.-P.; Nédélec, J.-Y. Tetrahedron 2002, 58, 271.
208. Léonel, E.; Paugam, J.-P.; Condon-Gueugnot, S.; Nédélec, J.-Y. Tetrahedron 1998, 54, 3207.
209. Oudeyer, S.; Léonel, E.; Paugam, J.-P.; Nédélec, J.-Y. Tetrahedron 2003, 59, 1073.
210. Oudeyer, S.; Léonel, E.; Paugam, J.-P.; Sulpice-Gaillet, C.; Nédélec, J.-Y. Tetrahedron 2006, 62, 1583.
211. Duñach, E.; Périchon, J. J. Organomet. Chem. 1988, 352, 239.
212. Labbé, E.; Duñach, E.; Périchon, J. J. Organomet. Chem. 1988, 353, C51.
213. Duñach, E.; Derien, S.; Périchon, J. J. Organomet. Chem. 1989, 364, C33.
214. Derien, S.; Duñach, E.; Périchon, J. J. Am. Chem. Soc. 1991, 113, 8447.
215. Derien, S.; Duãch, E.; Périchon, J. J. Organomet. Chem. 1990, 385, C43.
216. Derien, S.; Clinet, J.-C.; Duẽnach, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1991, 549.
217. Derien, S.; Clinet, J.-C.; Duẽnach, E.; Périchon, J. J. Organomet. Chem. 1992, 424, 213.
218. Derien, S.; Clinet, J.-C.; Duñach, E.; Périchon, J. Tetrahedron 1992, 48, 5235.
219. Derien, S.; Clinet, J.-C.; Duñach, E.; Perichon, J. J. Org. Chem. 1993, 58,2578.
220. Derien, S.; Clinet, J.-C.; Duñach, E.; Périchon, J. Synlett 1990, 361.
221. Condon-Gueugnot, S.; Léonel, E.; Nédélec, J.-Y.; Périchon, J. J. Org. Chem. 1995, 60, 7684.
222. Condon, S.; Nédélec, J.-Y.; Périchon, J. Eur. J. Org. Chem. 2002, 105.
223. Condon, S.; Dupré, D.; Lachaise, I.; Nédélec, J.-Y. Synthesis 2002, 1752.
224. Condon-Gueugnot, S.; Dupré, D.; Nédélec, J.-Y.; Périchon, J. Synthesis 1997, 1457.
225. Métay, E.; Léonel, E.; Condon, S.; Nédélec, J.-Y. Tetrahedron 2006, 62, 8515.
226. de Mendonga Cavalcanti, J. C.; Goulart, M. O. F.; Léonel, E.; Nédélec, J.-Y. Tetrahedron Lett. 2002, 43, 6343.
227. Gomes, P.; Gosmini, C.; Médélec, J.-Y.; Périchon, J. Tetrahedron Lett. 2002, 43, 5901.
228. Jia, C.; Fujiwara, Y. Pure Appl. Chem. 2001, 73, 319.
229. Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586.
230. Amatore, C.; Cammoun, C.; Jutand, A. Adv. Synth. Catal. 2007, 349, 292.
231. For a review on orthometallation, see: Pfeffer, M. Pure Appl. Chem. 1992, 64, 335.
232. Heck, R. F. J. Am. Chem. Soc. 1969, 91, 6707.
233. Grennberg, H.; Gogoll, A.; Bäckvall, J.-E. Organometallics 1993, 12, 1790.
234. Amatore, C.; Cammoun, C.; Jutand, A. Synlett 2007, 2173.
235. Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185.
236. Steinhoff, B. A.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 4348.
237. Bäckvall, J.-E.; Gogoll, A. J. Chem. Soc., Chem. Commun. 1987, 1237.
238. Bäckvall, J.-E.; Åkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411.
239. Inokuchi, T.; Ping, L.; Hamaue, F.; Izawa, M.; Torii, S. Chem. Lett. 1994, 121.
240. Mitsudo, K.; Kaide, T.; Nakamoto, E.; Yoshida, K.; Tanaka, H. J. Am. Chem. Soc. 2007, 129, 2246.
241. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
242. Mehrman, S. T.; Abdel-Magid, A. F.; Maryanoff, C. A.; Medaer, B. P. Topics III, Organometallic Chemistry 06, Organometallics in Process Chemistry; Larsen, R. D., Ed.; Springer-Verlag: Berlin-Heidelberg, 2004; p 153.
243. Gao, Y.; Zepp, C. M.; Wai, J. S. M. Abstr. Pap. Am. Chem. Soc. 1990, 199, 15.
244. Gao, Y.; Zepp, C. M. World Patent WO9317150 1993.
245. Torii, S.; Liu, P.; Tanaka, H. Chem. Lett. 1995, 319.
246. Torii, S.; Liu, P.; Bhuvaneswari, N.; Amatore, C.; Jutand, A. J. Org. Chem. 1996, 61, 3055.
247. Amatore, C.; Carré, E.; Jutand, A.; Tanaka, H.; Torii, S.; Chiarotto, I.; Carelli, I. Electrochim. Acta 1997, 42, 2143.