Electron transfer in organonickel complexes of α-diimines: Versatile redox catalysts for C-C or C-P coupling reactions - A review

Journal of Organometallic Chemistry

Volumn 692, Issue 15, 2007, Pages 3156-3166

  Klein, Axel ^a   Budnikova, Yulia H ^b   Sinyashin, Oleg G ^b  

^a UNIVERSITY OF COLOGNE   (Germany)

^b A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

Diimine ligands; C C coupling reactions; Electrocatalysis; Electrochemistry; Organonickel; Spectroelectrochemistry

Indexed keywords

CATALYSTS; CHEMICAL BONDS; COMPLEXATION; ELECTROCATALYSIS; ELECTRON TRANSPORT PROPERTIES; LIGANDS; ORGANOMETALLICS; REDOX REACTIONS; SPECTROELECTROCHEMISTRY;

COUPLING REACTIONS; ELECTROSYNTHESIS; OXIDATIONS STATE;

NICKEL COMPOUNDS;

EID: 34250189541     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2007.01.021     Document Type: Article

References (80)

1. In: Tamaru Y. (Ed). Modern Organonickel Chemistry (2005), Wiley-VCH, Weinheim
2. In: de Meijere A., and Diederich F. (Eds). Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. (2004), Wiley-VCH, Weinheim
3. Beletskaya I.P., and Cheprakov A.V. In: McCleverty J.A., and Meyer T.J. (Eds). Comprehensive Coordination Chemistry II (2004), Elsevier, Oxford, UK 305
4. Stadler A., and Kappe C.O. Org. Lett. 4 (2002) 3541
5. Wolf J., Labande A., Natella M., Daran J.-C., and Poli R. J. Mol. Catal. A 259 (2006) 205
6. Gavryushin A., Kofink C., Manolikakes G., and Knochel P. Tetrahedron 62 (2006) 7521
7. Anderson T.J., and Vicic D.A. Organometallics 23 (2004) 623
8. Bercot E.A., and Rovis T. J. Am. Chem. Soc. 127 (2004) 247
9. Moinet C., Hurvois J.-P., and Jutand A. Adv. Org. Synth. 1 (2005) 403
10. Nédélec J.-Y., Périchon J., and Troupel M. Top. Curr. Chem. 185 (1997) 141
11. Budnikova Y.H. Russ. Chem. Rev. 71 (2002) 111
12. de Franca K.W.R., de Lira Oliveira J., Florencio T., Da Silva A.P., Navarro M., Léonel E., and Nédélec J.-Y. J. Org. Chem. 70 (2005) 10778
13. de Franca K.W.R., Navarro M., Léonel E., Durandetti M., and Nédélec J.-Y. J. Org. Chem. 67 (2002) 1838
14. Durandetti M., and Périchon J. Synthesis (2004) 3079
15. Raynal F., Barhdadi R., Périchon J., Savall A., and Troupel M. Adv. Synth. Catal. 344 (2002) 45
16. Durandetti M., Nedelec J.-Y., and Périchon J. J. Org. Chem. 61 (1996) 1748
17. Yakhvarov D.G., Budnikova Y.H., and Sinyashin O.G. Russ. J. Electrochem. 39 (2003) 1261
18. Budnikova Y.H., Kargin Y.M., Nédélec J.-Y., and Périchon J. J. Organomet. Chem. 575 (1999) 63
19. Yakhvarov D.G., Budnikova Y.H., and Sinyashin O.G. Mendeleev Commun. (2002) 175
20. Amatore C., Jutand A., Périchon J., and Rollin Y. Monatsh. Chem. 131 (2000) 1293
21. Gosmini C., Nédélec J.-Y., and Périchon J. Tetrahedron Lett. 41 (2000) 5039
22. Gosmini C., Nédélec J.-Y., and Périchon J. Tetrahedron Lett. 41 (2000) 201
23. Gosmini C., Lasry S., Nédélec J.-Y., and Périchon J. Tetrahedron 54 (1998) 1289
24. Meyer G., Troupel M., and Périchon J. J. Organomet. Chem. 393 (1990) 137
25. Courtois V., Barhdadi R., Troupel M., and Périchon J. Tetrahedron 53 (1997) 11569
26. Sengmany S., Léonel E., Paugam J.P., and Nédélec J.-Y. Tetrahedron 58 (2002) 271
27. Ocafrain M., Dolhem E., Nédélec J.-Y., and Troupel M. J. Organomet. Chem. 571 (1998) 37
28. Da Silva A.P., Mota S.D.C., Bieber L.W., and Navarro M. Tetrahedron 62 (2006) 5435
29. Da Silva A.P., Maia A.C.S., and Navarro M. Tetrahedron Lett. 46 (2005) 3233
30. Goken D.M., Peters D.G., Karty J.A., and Reilly J.P. J. Electroanal. Chem. 564 (2004) 123
31. Franco D., Wenger K., Antonczak S., Cabrol-Bass D., Dunach E., Rocamora M., Gomez M., and Muller G. Chem. Eur. J. 8 (2002) 664
32. Olivero S., Franco D., Clinet J.-C., and Dunach E. Coll. Czech. Chem. Commun. 65 (2000) 844
33. Tascedda P., and Dunach E. Chem. Commun. (2000) 449
34. Dérien S., Dunach E., and Périchon J. J. Am. Chem. Soc. 113 (1991) 8447
35. Dérien S., Clinet J.-C., Dunach E., and Périchon J. J. Chem. Soc., Chem. Commun. (1991) 549
36. Dérien S., Clinet J.-C., Dunach E., and Périchon J. Synlett (1990) 361
37. Kuang C., Yang Q., Senbuko H., and Tokuda M. Chem. Lett. 34 (2005) 528
38. Bond A.M. Broadening Electrochemical Horizons (2002), Oxford University Press
39. Amatore C., Arbault S., Maisonhaute E., Szunerits S., and Thouin L. Electrochemistry at ultramicroelectrodes: small and fast may be useful. In: Pombeiro A.J.L., and Amatore C. (Eds). Trends in Molecular Electrochemistry (2004), FontisMedia S.A., Lausanne 385
40. Alessio E., Daff S., Elliot M., Iengo E., Jack L.A., Macnamara K.G., Pratt J.M., and Yellowlees L.J. Spectroelectrochemical techniques. In: Pombeiro A.J.L., and Amatore C. (Eds). Trends in Molecular Electrochemistry (2004), FontisMedia S.A., Lausanne 339
41. Kaim W. From electron transfer to chemistry: electrochemical analysis of organometallic reaction centers and of their interaction across ligand bridge. In: Pombeiro A.J.L., and Amatore C. (Eds). Trends in Molecular Electrochemistry (2004), FontisMedia S.A., Lausanne 127
42. McCleverty J.A., and Ward M.D. Mono- and dinuclear molybdenum and tungsten complexes: electrochemistry, optics and magnetics. In: Pombeiro A.J.L., and Amatore C. (Eds). Trends in Molecular Electrochemistry (2004), FontisMedia S.A., Lausanne 71
43. Pombeiro A.J.L., and Guedes da Silva M.F. Bond and structure activation by anodic electron-transfer: metal-hydrogen bond cleavage and cis/trans isomerization in coordination compounds. In: Pombeiro A.J.L., and Amatore C. (Eds). Trends in Molecular Electrochemistry (2004), FontisMedia S.A., Lausanne 153
44. Chaudhuri P., Verani C.N., Bill E., Bothe E., Weyhermüller T., and Wieghardt K. J. Am. Chem. Soc. 123 (2001) 2213
45. Chiusoli G.P., and Salerno G. Synthetic applications of organonickel complexes in organic chemistry. Adv. Organomet. Chem. 17 (1979) 195
46. Jolly P.W., and Wilke G. The Organic Chemistry of Nickel. Part 2. Organic Synthesis (1975), Academic Press, New York p. 416
47. Kochi J.K. Organometallic Mechanisms and Catalysis (1978), Academic Press, New York p. 623
48. Zilbermann I., Maimon E., Cohen H., and Meyerstein D. Chem. Rev. 105 (2005) 2609
49. Amatore C., and Jutand A. Organometallics 7 (1988) 2203
50. Amatore C., Jutand A., and Mottier L. J. Electroanal. Chem. 306 (1991) 125
51. Amatore C., and Jutand A. J. Am. Chem. Soc. 113 (1991) 2819
52. The conversion factors between various reference electrodes are taken from:. Connelly N.G., and Geiger W.E. Chem. Rev. 96 (1996) 877
53. Budnikova Y.H., Périchon J., Yakhvarov D.G., Kargin Y.M., and Sinyashin O.G. J. Organomet. Chem. 630 (2001) 185
54. Durandetti M., Devaud M., and Périchon J. New. J. Chem. 20 (1996) 659
55. Yamamoto T., Wakabayashi S., and Osakada K. J. Organomet. Chem. 428 (1992) 228
56. Cannes C., Labbe E., Durandetti M., Devaud M., and Nédélec J.-Y. J. Electroanal. Chem. 412 (1996) 85
57. Yakhvarov D.G., Tazeev D.I., Sinyashin O.G., Giambastiani G., Bianchini C., Segarra A.M., Lönnecke P., and Hey-Hawkins E. Polyhedron 25 (2006) 1607
58. Yakhvarov D.G., Budnikova Y.H., and Sinyashin O.G. Russ. Chem. Bull. Int. Ed. 52 (2003) 567
59. Yakhvarov D.G., Samieva E.G., Tazeev D.I., and Budnikova Y.H. Russ. Chem. Bull. Int. Ed. 51 (2002) 796
60. Seidel W. Z. Chem. 25 (1985) 411
61. Klein A., Feth M.P., Bertagnolli H., and Záliš S. Eur. J. Inorg. Chem. (2004) 2784
62. Feth M.P., Klein A., and Bertagnolli H. Eur. J. Inorg. Chem. (2003) 839
63. Klein A. Z. Anorg. Allg. Chem. 627 (2001) 645
64. Klein A., Kaiser A., Sarkar B., Wanner M., and Fiedler J. Eur. J. Inorg. Chem. (2007) 10.1002/ejic.200600865
65. Uchino M., Asagi K., Yamamoto A., and Ikeda S. J. Organomet. Chem. 84 (1975) 93
66. Yamamoto T., Abla M., and Murakami Y. Bull. Chem. Soc. Jpn. (2002) 1997
67. Tsou T.T., and Kochi J.K. J. Am. Chem. Soc. 101 (1979) 6319
68. Chardon-Noblat S., Deronzier A., and Ziessel R. Collect. Czech. Chem. Commun. 66 (2001) 207
69. Chardon-Noblat S., Deronzier A., Hartl F., van Slageren J., and Mahabiersing T. Eur. J. Inorg. Chem. (2001) 613
70. Chardon-Noblat S., Cripps G.H., Deronzier A., Field J.S., Gouws S., Haines R., and Southway F. Organometallics 20 (2001) 1668
71. Chardon-Noblat S., Deronzier A., Ziessel R., and Zsoldos D. Inorg. Chem. 36 (1997) 5384
72. Baumann F., Kaim W., Denninger G., Kümmerer H.-J., and Fiedler J. Organometallics 24 (2005) 1966
73. Dogan A., Sarkar B., Klein A., Lissner F., Schleid Th., Fiedler J., Záliš S., Jain V.K., and Kaim W. Inorg. Chem. 43 (2004) 5973
74. Berger S., Fiedler J., Reinhardt R., and Kaim W. Inorg. Chem. 43 (2004) 1530
75. Paolucci F., Marcaccio M., Paradisi C., Roffia S., Bignozzi C.A., and Amatore C. J. Phys. Chem. B 102 (1998) 4759
76. Amatore C., and Jutand A. Acc. Chem. Res. 33 (2000) 314
77. 2(bpy)].
78. Krejči{dotless}́k M., Záliš S., Ladwig M., Matheis W., and Kaim W. J. Chem. Soc., Perkin Trans. (1992) 2007
79. Le Gall E., Troupel M., and Nédélec J.-Y. Tetrahedron 59 (2003) 7497
80. Le Gall E., Ben Aissi K., Lachaise I., and Troupel M. Synlett (2006) 954