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New Efficient Catalytic Processes in Water: An Environmental Bening Solvent

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New Methodologies and Techniques for a Sustainable Organic Chemistry

Part of the book series: NATO Science Series II: Mathematics, Physics and Chemistry ((NAII,volume 246))

Water has attracted significant attention as an alternative solvent for transition metal-catalyzed reactions because it is non-toxic, non flammable solvent. The use of water as solvent allows simplified procedures for separation of the catalyst from the products and recycling the catalyst. This type of catalysis contributes to the concept of green chemistry. This chapter will focus on old and recent developments in the design and applications of some aqueous phase palladium, rhodium, platinum, and ruthenium reactions which have a great academic and industrial interest.

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References

  1. R. A. Sheldon, Chemtech 24(3), 38–47 (1994).

    CAS  Google Scholar 

  2. J. O. Metzger et al., Angew. Chem. Int. Ed. 41, 414–436 (2002).

    Article  Google Scholar 

  3. Special issue: Green Chemistry. Acc. Chem. Res., 35, 685–811 (2002).

    Google Scholar 

  4. P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford Press, New York (2000).

    Google Scholar 

  5. TPPMS: S. Ahrland, J. Chatt, N. R. Davies, and A. A. Williams, J. Chem. Soc. 276 (1958).

    Google Scholar 

  6. TPPTS: (a) E. Kuntz, Homogeneous catalysis in water, Chemtech 570–575 (1987); (b) E. Kuntz, Rhone-Poulenc Industrie FB 2366.237 (1976); (c) G. Mignani, D. Morel, and Y. Colleuille, Tetrahedron Lett. 26, 6337–6340 (1985).

    Google Scholar 

  7. B. Cornils, J. Hibbel, W. Konkol, J. Much, V. Schmid, and E. Webus, A. G. Ruhrchemie, German patent (1982), n° DE-B 3 234 701. 2 Rhône-Poulenc, European patent (1980) N° EP 44 771 and 1991 N° EP 441 708.

    Google Scholar 

  8. J. M. Grosselin, C. Mercier, G. Allmang, and F. Grass, Organometallics 10, 2126–2133 (1991).

    Article  CAS  Google Scholar 

  9. (a) N. A. Bumagin, P. G. More, and I. P. Beletskaya, J. Organomet. Chem. 371, 397–401 (1989); (b) N. A. Bumagin, V. V. Bykov, L. I. Sukhomlinova, T. Tolstaya, and I. P. Beletskaya, J. Organomet. Chem. 486, 259–262 (1995).

    Google Scholar 

  10. A. L. Casalnuovo, and J. C. Calabrese, J. Am. Chem. Soc. 112, 4324–4330 (1990).

    Article  CAS  Google Scholar 

  11. J. P. Genet, E. Blart, and M. Savignac, Synlett 715–717 (1992).

    Google Scholar 

  12. Books: (a) Organic Reactions in Aqueous Media, C. J. Li and T. H. Chan (eds), Wiley, New York. (1997); (b) Organic Synthesis in Water, P. A. Grieco (ed.), Blackie Academic & Professional, London (1998).

    Google Scholar 

  13. Reviews: (a) W. A. Herrmann and C. W. Kohlpaintner, Angew. Chem. Int. Ed. 32, 1524–1544 (1993); (b) J. P. Genet and M. Savignac, J. Organomet. Chem. 576, 305–317 (1999); (c) A. Lubineau and J. Augé, Topics in Current Chemistry, Vol. 206, Springer, Berlin (1999); (d) J. P. Genet, M. Savignac, and S. Lemaire-Audoire, Monographs, Transition Metal Catalyzed Reactions, A chemistry for the 21st century, S.-I. Murahashi and S. G. Davies (eds) 55–79 (1999); (e) N. Pinault and D. W. Bruce, Coord. Chem. Rev. 241, 1–25 (2003); (f) V. Michelet, M. Savignac and J. P. Genet, Electronic Encyclopedia of Reagents for Organic Synthesis, Wiley, Chichester (2004); (g) C.-J. Li, Chem. Rev. 105, 3095–3165 (2005); (h) K. H. Shaughnessy and R. B. De Vasher, Curr. Org. Chem. 9, 585–604 (2005).

    Google Scholar 

  14. Books: (a) J. Tsuji, Palladium Reagents and Catalysts, Wiley, New York (1995); (b) Handbook of Organopalladium. Chemistry for organic syntheses (2 vol) E. Negishi (ed.), Wiley, NewYork (2002).

    Google Scholar 

  15. (a) TPPTC: V. Michelet, R. Amengual, and J. P. Genet, Adv. Synth. Catal. 344, 393–398 (2002); (b) E. Genin, R. Amengual, V. Michelet, M. Savignac, A. Jutand, L. Neuville, and J. P. Genet, Adv. Synth. Catal. 346, 1733–1741 (2004).

    Google Scholar 

  16. GUAPHOS: (a) A. Hessler, O. Stelzer, H. Dibowski, K. Worm, and F. P. Schmidtchen, J. Org. Chem. 62, 2362–2369 (1997); (b) P. Machnitzki, M. Tepper, K. Wenz, O. Stelzer, and E. Herdtweck, J. Organomet. Chem. 602, 158–169 (2000).

    Google Scholar 

  17. TPPTP: W. J. Dressick, C. George, S. L. Brandow, T. L. Schull and D. A. Knight, J. Org. Chem. 65, 5059–5062 (2000).

    Article  CAS  Google Scholar 

  18. O. Herd, A. Hessler, K. P. Langhans, and O. Stelzer, J. Organomet. Chem. 475, 99–111 (1994).

    Article  CAS  Google Scholar 

  19. TXPS: L. R. Moore and K. H. Shaughnessy, Org. Lett. 2, 225–228 (2004); see also: H. Gulyas, A. Szollosy, B. E. Hanson, and J. Bakos, Tetrahedron Lett. 43, 2543–2546 (2002).

    Article  Google Scholar 

  20. W. Chen, L. Xu, and J. Xiao, Org. Lett., 2, 2675–2677 (2000).

    Article  CAS  Google Scholar 

  21. O. Herd, A. Hessler, K. P. Langhans, O. Stelzer, N. Weferling, and W. S. Sheldrick, Angew. Chem. Int. Ed. Engl. 32, 1058–1059 (1993).

    Article  Google Scholar 

  22. L. Caron, M. Canipelle, S. Tilloy, H. Bricourt, and E. Monflier, Tetrahedron Lett. 42(20), 8897–8840 (2001).

    Google Scholar 

  23. K. Anderson and S. L. Buchwald, Angew. Chem. Int. Ed. 44, 6173–6177 (2005).

    Article  CAS  Google Scholar 

  24. C. Amatore, E. Blart, J. P. Genet, A. Jutand, S. Lemaire-Audoire, and M. Savignac, J. Org. Chem. 60(21), 6829–6839 (1995); see also G. Papadogiarnakis, J. A. Peters, L. Maat, and R. A. Sheldon, J. Chem. Soc. Chem. Commun. 1105–1105 (1995).

    Article  CAS  Google Scholar 

  25. S. Lemaire-Audoire, M. Savignac, C. Dupuis, and J. P. Genet Tetrahedron Lett. 37, 2003–2006 (1996).

    Article  CAS  Google Scholar 

  26. R. Métivier, R. Amengual, I. Leray, V. Michelet, and J. P. Genet, Org. Lett. 6, 739–742 (2004).

    Article  Google Scholar 

  27. (a) E. Blart, J. P. Genet, M. Savignac, M. Safi, and D. Sinou, Tetrahedron 50, 505–514 (1993); (b) M. Safi and D. Sinou, Tetrahedron Lett. 32, 2025–2028 (1991).

    Google Scholar 

  28. J. P. Genet, E. Blart, M. Savignac, S. Lemeune and J. M. Paris, Tetrahedron Lett. 34(26) 4189–4192 (1993).

    Article  CAS  Google Scholar 

  29. (a) J. P. Genet, E. Blart, M. Savignac, S. Lemaire-Audoire, J. M. Paris, and J. M. Bernard, Tetrahedron 50(2), 497–503 (1994); (b) S. Lemaire-Audoire, J. P. Genet, and M. Savignac, Tetrahedron Lett. 35(47) 8783–8786 (1994); (c) S. Lemaire-Audoire, J. P. Genet, M. Savignac, G. Pourcelot, and J. M. Bernard, J. Mol. Cat. A, Chem. 116, 247–258 (1997).

    Google Scholar 

  30. S. Lemaire-Audoire, J. P. Genet and M. Savignac, Tetrahedron Lett. 38(17), 2955–2958 (1997).

    Article  CAS  Google Scholar 

  31. H. Kinoshita, H. Shinokubo, and K. Oshima, Angew. Chem. Int. Ed. 44, 2397–2400 (2005).

    Article  CAS  Google Scholar 

  32. V. Michelet, J. C. Galland, M. Savignac, and J. P. Genet, Org. Lett. 3, 2065–2067 (2001).

    Article  CAS  Google Scholar 

  33. J. C. Galland, M. Savignac and J. P. Genet, Tetrahedron Lett. 38(50) 8695–8698 (1987).

    Article  Google Scholar 

  34. C. Nevado, L. Charruault, V. Michelet, C. Nieto-Oberhuber, M. Paz Muñoz, M. Méndez, M. N. Rager, J. P. Genet, and A. M. Echavarren, Eur. J. Org. Chem. 706–713 (2003).

    Google Scholar 

  35. L. Charruault, V. Michelet, R. Taras, S. Gladiali, and J. P. Genet, Chem. Commun. 850–851 (2004).

    Google Scholar 

  36. (a) L. Charruault, V. Michelet, and J. P. Genet, Tetrahedron Lett. 43, 4757–4760 (2002); (b) J. C. Galland, S. Dias, M. Savignac, and J. P. Genet, Tetrahedron 57, 5137–5148 (2001); (c) L. Charruault, V. Michelet, and J. P. Genet, Tetrahedron Lett. 43, 4757–4760 (2002).

    Google Scholar 

  37. Review: N. Miyaura and A. Suzuki, Chem. Rev. 95, 2457–2483 (1995).

    Article  CAS  Google Scholar 

  38. D. Larsen, A. O. King, C. Y. Chen, E. G. Corley, B. S. Foster, F. E. Roberts, C. Yang, D. R. Lieberman, R. A. Reamer, D. M. Tschaen, T. R. Verhoeven, P. J. Reider, Y. S. Lo, L. T. Rossano, A. S. Brookes, D. Meloni, J. R. Moore, and J. F. Arnett, J. Org. Chem. 59, 6391–6394 (1994).

    Article  CAS  Google Scholar 

  39. Y. Kishi, J. I. Venishi, J. M. Beau, and R. W. Amstrong, J. Am. Chem. Soc. 109, 4756–4758 (1987).

    Article  Google Scholar 

  40. N. A. Bumagin, V. V. Bykov, and I. P. Beletskaya, IZV. Akad. Nauk. SSSR Ser. Kim 237 (1989).

    Google Scholar 

  41. H. Sakurai, T. Tsukuda, and T. Hirao, J. Org. Chem. 67, 2721–2722 (2002).

    Article  CAS  Google Scholar 

  42. T. I. Wallow and B. Novak, J. Am. Chem. Soc. 7411–7412 (1991).

    Google Scholar 

  43. (a) K. H. Shaughnessy and R. S. Booth, Org. Lett. 3(17), 2717–2759 (2001); (b) T. Kang, Q. Feng, and M. Luo, Synlett 15, 2305–2308 (2005).

    Google Scholar 

  44. C. Dupuis, L. Charruault, M. Savignac, V. Michelet, K. Adiey, and J. P. Genet, Tetrahedron Lett. 42, 6523–6526 (2001).

    Article  CAS  Google Scholar 

  45. E. Blart, V. Mouries, A. Linquist, M. Savignac, J. P. Genet, and M. Vaultier, Tetrahedron Lett. 36, 1443–1446 (1995).

    Article  Google Scholar 

  46. A. K. Mapp and C. H. Heathcock, J. Org. Chem. 64, 23–27 (1999).

    Article  CAS  Google Scholar 

  47. E. Patzold and G. Ohme, J. Mol. Cat. A: Chem. 152, 69–76 (2000).

    Article  Google Scholar 

  48. S. Darses, T. Jeffery, J. L. Brayer, J. P. Demoute, and J. P. Genet, Tetrahedron Lett. 37, 3857–3860 (1996); S. Darses, T. Jeffery, J. L. Brayer, J. P. Demoute, and J. P. Genet, Bull. Soc. Chim. Fr. 133, 1095–1102 (1996).

    CAS  Google Scholar 

  49. D. M. Willis and R. N. Strongin, Tetrahedron Lett. 41, 6271–6274 (2000).

    Article  CAS  Google Scholar 

  50. G. Fu and A. Littke, Angew. Chem. Int. Ed. 3387–3388 (1998); For a recent Suzuki coupling of aryl chlorides using Pd/C in water and microwave assisted reaction: R. K. Arvela and N. E. Leadbeater, Org. Lett. 7, 11, 2101 (2005) and references cited therein.

    Google Scholar 

  51. (a) S. Darses, G. Michaud, and J. P. Genet, Eur. J. Org. Chem. 1875–1887 (1999); (b) S. Darses, G. Michaud, and J. P. Genet, Tetrahedron Lett. 39, 5045–5048 (1998).

    Google Scholar 

  52. K. Puenteuer, M. Scalone (Hoffmann-La Roche A. G.) Pat. EP 1057831A, May 2000.

    Google Scholar 

  53. (a) R. A. Batey and T. D. Qauch, Tetrahedron Lett. 42, 7601–7604 (2002); (b) G. A. Molander and C. R. Bernardi, J. Org. Chem. 67, 8424–8429 (2002); (c) T. E. Barder and S. L. Buchwald, Org. Lett. 6(16), 2649–2652 (2004).

    Google Scholar 

  54. (a) S. Saito, M. Sakai, and N. Miyaura, Tetrahedron Lett. 37, 2993–2996 (1996); (b) A. F. Indolese, Tetrahedron Lett. 38, 3513–3516 (1997).

    Google Scholar 

  55. J. C. Galland, M. Savignac, and J. P. Genet, Tetrahedron Lett. 40, 2323–2326 (1999).

    Article  CAS  Google Scholar 

  56. D. R. Tuetin, A. M. Echavarren, and J. K. Stille, Tetrahedron 45, 979–992 (1989).

    Article  Google Scholar 

  57. H. C. Zhang and G. D. Davis, Jr., Organometallics 12, 1499–1500 (1993).

    Article  CAS  Google Scholar 

  58. R. Rai, K. B. Aubrecht, and D. B. Collum, Tetrahedron Lett. 36, 3111–3114 (1995).

    Article  CAS  Google Scholar 

  59. Review: K. Fagnou and M. Lautens, Chem. Rev. 103, 169–196 (2003).

    Article  CAS  Google Scholar 

  60. Review: S. Darses and J. P. Genet, Eur. J. Org. Chem. 4313–4327 (2003).

    Google Scholar 

  61. (a) A. Furstner and H. Karuse, Adv. Synth. Catal. 4, 343–350 (2001); (b) C. Moreau, C. Hagne, A. S. Weller, and C. Frost, Tetrahedron Lett. 42, 6957–6960 (2001); (c) R. Huang and K. H. Shaughnessy, Chem. Commun. 4484–4486 (2005).

    Google Scholar 

  62. R. A. Batey, A. N. Thadani, and D. V. Smil, Org. Lett. 1, 1683–1686 (1999).

    Article  CAS  Google Scholar 

  63. M. Pucheault, S. Darses, and J. P. Genet, Chem. Commun. 4714–4716 (2005).

    Google Scholar 

  64. T. Hayashi, J. W. Han, and N. Tokunaga, J. Am. Chem. Soc. 123, 12915–12916 (2001).

    Article  Google Scholar 

  65. M. Lautens and M. Yoshida, Org. Lett. 4, 123–125 (2002).

    Article  CAS  Google Scholar 

  66. E. Genin, V. Michelet, and J. P. Genet, Tetrahedron Lett. 45, 4157–4161 (2004); Ibid. J. Organomet. Chem. 689, 3820–3830 (2004).

    Article  CAS  Google Scholar 

  67. V. Michelet, R. Amengual, and J. P. Genet, Tetrahedron Lett. 43, 5905–5908 (2002).

    Article  Google Scholar 

  68. R. Itooka, Y. Iguchi, and N. Miyaura, Chem. Lett. 722–723 (2001).

    Google Scholar 

  69. Review: (a) T. Hayashi, Synlett 879–887 (2001); (b) T. Hayashi and K. Yamasaki, Chem. Rev. 103, 2829–2844 (2003); For a recent paper see F. X. Chen, A. Kina, T. Hayashi, Org. Lett. 8(2), 341–344 (2006).

    Google Scholar 

  70. R. Amengual, V. Michelet, and J. P. Genet, Synlett 1791–1794 (2002).

    Google Scholar 

  71. S. Darses, M. Pucheault, and J. P. Genet, Eur. J. Org. Chem. 3552–3557 (2002); S. Darses, G. Michaud, and J. P. Genet, Tetrahedron Lett. 43, 6155–6157 (2002).

    Article  Google Scholar 

  72. M. Pucheault, L. Navarre, S. Darses, and J. P. Genet, Tetrahedron Lett. 46, 4247–4250 (2005).

    Article  Google Scholar 

  73. (a) D. Sinou, Adv. Synth. Catal. 344(3), 221–237 (2002); (b) Q. H. Fan, D. Y. M. Li and A. S. C. Chan, Chem. Rev. 102(10), 3385–3466 (2002).

    Google Scholar 

  74. (a) R. H. Grubbs, R. H. Pine, in: Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, L. A. Paquette (eds), Pergamon Press, NewYork, Chapter 9.3 (1991); (b) K. C. Nicolaou, P. Q. Bulger, and D. Sarlah, Angew. Chem. Int. Ed. 44, 4490–4527 (2005).

    Google Scholar 

  75. (a) T. A. Kirkland, D. M. Lynn, and R. H. Grubbs, J. Org. Chem. 63, 9904–9909 (1998); (b) T. Rölle and R. H. Grubbs, Chem. Commun. 1070–1071 (2002).

    Google Scholar 

  76. K. Fuji, T. Morimoto, K. Tsutsumi, and K. Kakiuchi, Angew. Chem. Int. Ed. 42, 2409–2411 (2003).

    Article  CAS  Google Scholar 

  77. M. E. Kraft, J. A. Wright, and L. V. R. Bonaga, Tetrahedron Lett. 44, 3417–3422 (2003).

    Article  Google Scholar 

  78. L. Chen and C. J. Li, J. Org. Lett. 6, 3151–3153 (2004).

    Article  CAS  Google Scholar 

  79. (a) C. Wei and C. J. Li, J. Green Chem. 4, 39 (2002); (b) C. J. Li and C. Wei, Chem. Commun. 268–269 (2002); (c) J. Zhang, C. Wei, and C. J. Li, Tetrahedron Lett. 43, 5731–5733 (2002); (d) C. Wei and C. J. Li, J. Am. Chem. Soc. 125, 9584–9585 (2003).

    Google Scholar 

  80. (a) E. Mizushima, K. Sato, T. Hayashi, and M. Tanaka, Angew. Chem. Int. Ed. 41(23), 4563–4565 (2002); (b) for AgCl catalyst in water (see X. Yao and C. J. Li), Org. Lett. 7(20), 4395–4398 (2005).

    Google Scholar 

  81. (a) M. S. Sigman, A. W. Fatland, and B. E. Eaton, J. Am. Chem. Soc. 120, 5130–5131 (1998); (b) A. W. Fatland and B. E. Eaton, Org. Lett. 2(19), 3131–3133 (2000).

    Google Scholar 

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Genet, JP. (2008). New Efficient Catalytic Processes in Water: An Environmental Bening Solvent. In: Mordini, A., Faigl, F. (eds) New Methodologies and Techniques for a Sustainable Organic Chemistry. NATO Science Series II: Mathematics, Physics and Chemistry, vol 246. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-6793-8_7

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