Pure and Applied Chemistry

Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 831-844

http://dx.doi.org/10.1351/pac200880050831

Organometallic catalysts in synthetic organic chemistry: From reactions in aqueous media to gold catalysis

References

• 1. (a). M. Eissen, J. O. Metzger, E. Schmidt, U. Schneidewind. Angew. Chem., Int. Ed. 41, 414 (2002); (http://dx.doi.org/10.1002/1521-3773(20020201)41:3<414::AID-ANIE414>3.0.CO;2-N)
• 1. (b). P. T. Anastas, J. C. Warner. Green Chemistry: Theory and Practice, Oxford University Press, New York (2000).
• 2. TPPMS: S. Ahrland, J. Chatt, N. R. Davies, A. A. Williams. J. Chem. Soc. 276 (1958).
• 3. (a). E. Kuntz. CHEMTECH 570 (1987);
• 3. (b). B. Cornils, J. Hibbel, W. Konkol, J. Much, V. Schmid, E. Webus. Ruhrchemie A.G. German patent no. DE-B 3 234 701.2 (1982), Rhone-Poulenc, European patent no. EP 44 771 (1980).
• 4. (a). A. L. Casalnuovo, J. C. Calabrese. J. Am. Chem. Soc. 112, 4324 (1990); (http://dx.doi.org/10.1021/ja00167a032)
• 4. (b). J.-P. Genet, E. Blart, M. Savignac. Synlett 715 (1992). (http://dx.doi.org/10.1055/s-1992-21465)
• 5. (a). C. J. Li, T. H. Chan. (Eds.). Organic Reactions in Aqueous Media, John Wiley, New York (1997);
• 5. (b). P. A. Grieco (Ed.). Organic Synthesis in Water, Blackie Academic, Glasgow (1998).
• 6. (a). W. A. Herrmann, C. W. Kohlpaintner. Angew. Chem., Int. Ed. 32, 1524 (1993); (http://dx.doi.org/10.1002/anie.199315241)
• 6. (b). J.-P. Genet, M. Savignac. J. Organomet. Chem. 576, 305 (1999); (http://dx.doi.org/10.1016/S0022-328X(98)01088-2)
• 6. (c). A. Lubineau, J. Auge. Top. Curr. Chem. 206, Springer-Verlag, Berlin (1999);
• 6. (d). J.-P. Genet, M. Savignac, S. Lemaire-Audoire. Monographs, Transition Metal Catalyzed Reactions, A Chemistry for the 21st Century, S.-I. Murahashi, S. G. Davies. (Eds.), 55 (1999);
• 6. (e). N. Pinault, D. W. Bruce. Coord. Chem. Rev. 241, 1 (2003); (http://dx.doi.org/10.1016/S0010-8545(02)00306-5)
• 6. (f). V. Michelet, M. Savignac, J.-P. Genet. Electronic Encyclopedia of Reagents for Organic Synthesis, John Wiley, New York (2004);
• 6. (g). C.-J. Li. Chem. Rev. 105, 3095 (2005); (http://dx.doi.org/10.1021/cr030009u)
• 6. (h). K. H. Shaughnessy, R. B. De Vasher. Curr. Org. Chem. 9, 585 (2005). (http://dx.doi.org/10.2174/1385272053765042)
• 7. (a). O. Herd, A. Hessler, K. P. Langhans, O. Stelzer. J. Organomet. Chem. 475, 99 (1994); (http://dx.doi.org/10.1016/0022-328X(94)84012-1)
• 7. (b). L. R. Moore, K. H. Shaughnessy. Org. Lett. 5, 225 (2004); (http://dx.doi.org/10.1021/ol0360288)
• 7. (c). H. Gulyas, A. Szollosy, B. E. Hanson, J. Bakos. Tetrahedron Lett. 43, 2543 (2002); (http://dx.doi.org/10.1016/S0040-4039(02)00319-2)
• 7. (d). L. Caron, M. Canipelle, S. Tilloy, H. Bricourt, E. Monflier. Tetrahedron Lett. 42, 8837 (2001); (http://dx.doi.org/10.1016/S0040-4039(01)01918-9)
• 7. (e). K. W. Anderson, S. L. Buchwald. Angew. Chem., Int. Ed. 44, 6173 (2005). (http://dx.doi.org/10.1002/anie.200502017)
• 8. (a). A. Hessler, O. Stelzer, H. Dibowski, K. Worm, F. P. Schmidtchen. J. Org. Chem. 62, 2362 (1997); (http://dx.doi.org/10.1021/jo961140n)
• 8. (b). P. Machnitzki, M. Tepper, K. Wenz, O. Stelzer, E. Herdtweck. J. Organomet. Chem. 602, 158 (2000). (http://dx.doi.org/10.1016/S0022-328X(00)00151-0)
• 9. TPPTP: W. J. Dressick, C. George, S. L. Brandow, T. L. Schull, D. A. Knight. J. Org. Chem. 65, 5059 (2000). (http://dx.doi.org/10.1021/jo000371y)
• 10. W. Chen, L. Xu, J. Xiao. Org. Lett. 2, 2675 (2000). (http://dx.doi.org/10.1021/ol006203+)
• 11. (a). R. Amengual, E. Genin, V. Michelet, M. Savignac, J.-P. Genet. Adv. Synth. Catal. 344, 393 (2002); (http://dx.doi.org/10.1002/1615-4169(200206)344:3/4<393::AID-ADSC393>3.0.CO;2-K)
• 11. (b). E. Genin, R. Amengual, V. Michelet, M. Savignac, A. Jutand, L. Neuville, J.-P. Genet. Adv. Synth. Catal. 346, 1733 (2004); (http://dx.doi.org/10.1002/adsc.200404218)
• 11. (c). R. Amengual, V. Michelet, J.-P. Genet. Tetrahedron Lett. 43, 5905 (2002). (http://dx.doi.org/10.1016/S0040-4039(02)01274-1)
• 12. S. Tilloy, E. Genin, F. Hapiot, D. Landy, S. Fourmentin, J.-P. Genet, V. Michelet, E. Montflier. Adv. Synth. Catal. 346, 1547 (2006). (http://dx.doi.org/10.1002/adsc.200606160)
• 13. T. Hayashi, K. Inoue, N. Taniguchi, M. Osagawara. J. Am. Chem. Soc. 123, 9918 (2001). (http://dx.doi.org/10.1021/ja0165234)
• 14. (a). M. Lautens, M. Yoshida. Org. Lett. 4, 123 (2002); (http://dx.doi.org/10.1021/ol010261t)
• 14. (b). M. Lautens, M. Yoshida. J. Org. Chem. 68, 762 (2003). (http://dx.doi.org/10.1021/jo0205255)
• 15. H. Kinoshita, H. Shinobuko, K. Oshima. J. Am. Chem. Soc. 125, 7784 (2003). (http://dx.doi.org/10.1021/ja035438o)
• 16. (a). E. Genin, V. Michelet, J.-P. Genet. Tetrahedron Lett. 45, 415 (2004); (http://dx.doi.org/10.1016/j.tetlet.2004.03.136)
• 16. (b). E. Genin, V. Michelet, J.-P. Genet. J. Organomet. Chem. 689, 3820 (2004). (http://dx.doi.org/10.1016/j.jorganchem.2004.07.025)
• 17. E. Vedejs, R. W. Chapman, S. C. Fields, S. Lin, M. R Schrimpf. J. Org. Chem. 60, 3020 (1995). (http://dx.doi.org/10.1021/jo00115a016)
• 18. S. Darses, J.-P. Genet. Eur. J. Org. Chem. 4313 (2003). (http://dx.doi.org/10.1002/ejoc.200300294)
• 19. (a). G. A. Molander, R. Figueroa. Aldrichim. Acta 38, 49 (2005);
• 19. (b). G. A. Molander, N. Ellis. Acc. Chem. Res. 40, 275 (2007). (http://dx.doi.org/10.1021/ar050199q)
• 20. H. A. Stefani, R. Cella, A. S. Vieira. Tetrahedron 63, 3623 (2007). (http://dx.doi.org/10.1016/j.tet.2007.01.061)
• 21. S. Darses, J.-P. Genet. Chem. Rev. 108, 288 (2008). (http://dx.doi.org/10.1021/cr0509758)
• 22. (a). S. Darses, J.-P. Genet, G. Michaud. Tetrahedron Lett. 39, 5045 (1998); (http://dx.doi.org/10.1016/S0040-4039(98)01003-X)
• 22. (b). S. Darses, G. Michaud, J.-P. Genet. Eur. J. Org. Chem. 1875 (1999). (http://dx.doi.org/10.1002/(SICI)1099-0690(199908)1999:8<1875::AID-EJOC1875>3.0.CO;2-W)
• 23. A. R. Hunt, S. K. Stewart, A. Whiting. Tetrahedron Lett. 34, 3599 (1993). (http://dx.doi.org/10.1016/S0040-4039(00)73646-X)
• 24. K. Puentener, M. Scalone. (Hoffmann-La Roche AG), EP patent 1057831.
• 25. Review: K. Fagnou, M. Lautens. Chem. Rev. 103, 169 (2003). (http://dx.doi.org/10.1021/cr020007u)
• 26. R. A. Batey, A. N. Thadani, D. V. Smil. Org. Lett. 1, 1683 (1999). (http://dx.doi.org/10.1021/ol9910767)
• 27. (a). M. Pucheault, S. Darses, J.-P. Genet. Chem. Commun. 4714 (2005); (http://dx.doi.org/10.1039/b506245d)
• 27. (b). L. Navarre, S. Darses, J.-P. Genet. Adv. Synth. Catal. 348, 317 (2006). (http://dx.doi.org/10.1002/adsc.200505336)
• 28. M. Pucheault, S. Darses, J.-P. Genet. J. Am. Chem. Soc. 126, 15356 (2004). (http://dx.doi.org/10.1021/ja044749b)
• 29. (a). T. Hayashi. Synlett 879 (2001); (http://dx.doi.org/10.1055/s-2001-14657)
• 29. (b). T. Hayashi, K. Yamasaki. Chem. Rev. 103, 2829 (2003); (http://dx.doi.org/10.1021/cr020022z)
• 29. (c). T. Hayashi, M. Takahashi, Y. Takaya, M. Osagawara. J. Am. Chem. Soc. 124, 5052 (2002). (http://dx.doi.org/10.1021/ja012711i)
• 30. (a). S. Darses, M. Pucheault, J.-P. Genet. Eur. J. Org. Chem. 3552 (2002);
• 30. (b). S. Darses, G. Michaud, J.-P. Genet. Tetrahedron Lett. 43, 6155 (2002). (http://dx.doi.org/10.1016/S0040-4039(02)01288-1)
• 31. M. Pucheault, L. Navarre, S. Darses, J.-P. Genet. Tetrahedron Lett. 46, 4247 (2005). (http://dx.doi.org/10.1016/j.tetlet.2005.04.038)
• 32. T. Nishikata, Y. Yamamoto, N. Miyaura. Angew. Chem., Int. Ed. 42, 2768 (2003). (http://dx.doi.org/10.1002/anie.200350888)
• 33. M. T. Reetz, D. Moulin, A. Gosberg. Org. Lett. 3, 4083 (2001). (http://dx.doi.org/10.1021/ol010219y)
• 34. L. Navarre, S. Darses, J.-P. Genet. Angew. Chem., Int. Ed. 43, 719 (2004). (http://dx.doi.org/10.1002/anie.200352518)
• 36. L. Navarre, R. Martinez, S. Darses, J.-P. Genet. J. Am. Chem. Soc. In press.
• 36. (a). S. Duprat de Paule, S. Jeulin, V. Ratovelomanana-Vidal, J.-P. Genet, N. Champion, P. Dellis. Angew. Chem., Int. Ed. 43, 320 (2004); (http://dx.doi.org/10.1002/anie.200352453)
• 36. (b). S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-Vidal, J.-P. Genet, N. Champion, P. Dellis. Proc. Natl. Acad. Sci. USA 101, 5799 (2004). (http://dx.doi.org/10.1073/pnas.0307620101)
• 37. (a). B. M. Trost. Acc. Chem. Res. 23, 34 (1990); (http://dx.doi.org/10.1021/ar00170a004)
• 37. (b). B. M. Trost, M. J. Krische. Synlett 1 (1998); (http://dx.doi.org/10.1055/s-1998-1557)
• 37. (c). E. Negishi, C. Coperet, S. Ma, S. Y. Liou, F. Liu. Chem. Rev. 96, 365 (1996); (http://dx.doi.org/10.1021/cr950020x)
• 37. (d). I. Ojima, M. Tzamarioudaki, Z. Li, R. J. Donovan. Chem. Rev. 96, 635 (1996); (http://dx.doi.org/10.1021/cr950065y)
• 37. (e). C. Aubert, O. Buisine, M. Malacria. Chem. Rev. 3, 813 (2002); (http://dx.doi.org/10.1021/cr980054f)
• 37. (f). L. Anorbe, G. Dominguez, J. Perez-Castells. Chem.Eur. J. 10, 4938 (2004); (http://dx.doi.org/10.1002/chem.200400089)
• 37. (g). A. Furstner, P. W. Davies. Angew. Chem., Int. Ed. 46, 3410 (2007); (http://dx.doi.org/10.1002/anie.200604335)
• 37. (h). V. Michelet, P. Y. Toullec, J.-P. Genet. Angew. Chem., Int. Ed. (2007). In press.
• 39. J. C. Galland, M. Savignac, J.-P. Genet. Tetrahedron Lett. 38, 8695 (1997). (http://dx.doi.org/10.1016/S0040-4039(97)10337-9)
• 40. M. Mendez, M. Paz Munoz, A. Echavaren. J. Am. Chem. Soc. 122, 11549 (2000). (http://dx.doi.org/10.1021/ja002577m)
• 41. C. Nevado, L. Charruault, V. Michelet, C. Nieto-Oberhuber, M. Paz Munoz, M. Mendez, M. N. Rager, J.-P. Genet, A. M. Echavarren. Eur. J. Org. Chem. 706 (2003). (http://dx.doi.org/10.1002/ejoc.200390110)
• 41. (a). S. Lopez, E. N. Gomez, P. P. Galan, C. Nieto-Oberhuber, A. Echavarren. Angew. Chem., Int. Ed. 45, 6029 (2006); (http://dx.doi.org/10.1002/anie.200602448)
• 41. (b). C. A. Whitham, P. Mauleon, N. D. Shapiro, B. D. Sherry. J. Am. Chem. Soc. 129, 5838 (2007); (http://dx.doi.org/10.1021/ja071231+)
• 41. (c). A. Echavarren, E. J. Nunez. Chem.Eur. J. 12, 5916 (2006). (http://dx.doi.org/10.1002/chem.200600174)
• 43. L. Charruault, V. Michelet, R. Taras, S. Gladiali, J.-P. Genet. Chem. Commun. 850 (2004). (http://dx.doi.org/10.1039/b400908h)
• 43. (a). L. Charruault, V. Michelet, J.-P. Genet. Tetrahedron Lett. 43, 4757 (2002); (http://dx.doi.org/10.1016/S0040-4039(02)00908-5)
• 43. (b). J. C. Galland, S. Dias, M. Savignac, J.-P. Genet. Tetrahedron 57, 5137 (2001); (http://dx.doi.org/10.1016/S0040-4020(01)00368-4)
• 43. (c). L. Charruault, V. Michelet, J.-P. Genet. Tetrahedron Lett. 43, 4757 (2002). (http://dx.doi.org/10.1016/S0040-4039(02)00908-5)
• 44. (a). E. J. Jimenez-Nunez, A. Echavarren. Chem. Commun. 333 (2007); (http://dx.doi.org/10.1039/b612008c)
• 44. (b). A. S. K. Hashmi. Chem. Rev. 107, 3180 (2004); (http://dx.doi.org/10.1021/cr000436x)
• 44. (c). A. Hoffmann-Roder, N. Krause. Org. Biomol. Chem. 3, 387 (2005); (http://dx.doi.org/10.1039/b416516k)
• 44. (d). P. Pyykko. Angew. Chem., Int. Ed. 43, 4412 (2004); (http://dx.doi.org/10.1002/anie.200300624)
• 44. (e). S. Ma, S. Yu, Z. Gu. Angew. Chem., Int. Ed. 45, 200 (2006); (http://dx.doi.org/10.1002/anie.200502999)
• 44. (f). A. S. K. Hashmi, G. J. Hutchings. Angew. Chem., Int. Ed. 45, 7896 (2006); (http://dx.doi.org/10.1002/anie.200602454)
• 44. (g). A. Arcadi, S. Di Giuseppe. Curr. Org. Chem. 8, 795 (2004); (http://dx.doi.org/10.2174/1385272043370564)
• 44. (h). D. J. Gorin, F. D. Toste. Nature 446, 395 (2007). (http://dx.doi.org/10.1038/nature05592)
• 45. (a). E. Genin, L. Leseurre, P. Y. Toullec, J.-P. Genet, V. Michelet. Synlett 11, 1780 (2007);
• 45. (b). C. Nieto-Oberhuber, M. Paz Munoz, E. Bunuel, C. Nevado, D. J. Cardenas, A. Echavaren. Angew. Chem., Int. Ed. 43, 2402 (2004). (http://dx.doi.org/10.1002/anie.200353207)
• 47. L. Leseurre, P. Y. Toullec, J.-P. Genet, V. Michelet. Org. Lett. 9, 4049 (2007). (http://dx.doi.org/10.1021/ol7017483)
• 47. (a). P. Y. Toullec, E. Genin, L. Leseurre, J.-P. Genet, V. Michelet. Angew. Chem., Int. Ed. 45, 7427 (2006); (http://dx.doi.org/10.1002/anie.200601980)
• 47. (b). C. H. M. Amijs, C. Ferrer, A. Echavarren. Chem. Commun. 698 (2007). (http://dx.doi.org/10.1039/b615335f)
• 48. (a). E. Genin, S. Antoniotti, V. Michelet, P. Y. Toullec, C. Brancour, J.-P. Genet. J. Am. Chem. Soc. 128, 3112 (2006); (http://dx.doi.org/10.1021/ja056857j)
• 48. (b). E. Genin, S. Antoniotti, V. Michelet, P. Y. Toullec, C. Brancour, J.-P. Genet. Arkivoc 67 (2007).
• 50. E. Genin, S. Antoniotti, V. Michelet, J.-P. Genet. Angew. Chem., Int. Ed. 44, 4949 (2005). (http://dx.doi.org/10.1002/anie.200501150)
• 51. E. Genin, S. Antoniotti, V. Michelet, J.-P. Genet. J. Am. Chem. Soc. 127, 9976 (2005). (http://dx.doi.org/10.1021/ja0530671)
• 52. L. Yongfeng, Z. Feng, G. J. Forsyth. Angew. Chem., Int. Ed. 46, 279 (2007). (http://dx.doi.org/10.1002/anie.200601963)