Ultra-low catalyst loading as a concept in economical and sustainable modern chemistry: The contribution of ferrocenylpolyphosphane ligands

European Journal of Inorganic Chemistry

Volumn , Issue 24, 2007, Pages 3767-3780

  Hierso, Jean Cyrille ^a   Beaupérin, Matthieu ^a   Meunier, Philippe ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

Cross coupling; Ferrocenylphosphanes; Homogeneous catalysis; Multi dentate ligands; P ligands; Sustainable chemistry

Indexed keywords

CATALYSIS; CATALYSTS; LIGANDS; ORGANOMETALLICS;

CROSS-COUPLINGS; FERROCENYL; FERROCENYLPHOSPHANE; HOMOGENEOUS CATALYSIS; MULTIDENTATE LIGANDS; P LIGANDS; RENEWABLE FEEDSTOCKS; RESEARCH AREAS; SUSTAINABLE CHEMISTRY; ULTRA-LOW CATALYST LOADINGS;

SUSTAINABLE CHEMISTRY;

EID: 34548321029     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200700405     Document Type: Short Survey

References (60)

1. For instance, in Europe the COST program 2003-2006 "Sustainable Chemical Processes: Stereoselective Transition MetalCatalyzed Reaction", in the USA, the ACS-Green Chemistry Institute PRF programs, and since 2007, from the French Government, the ANR program "Chemistry and Processes for Sustainable Development".
2. P. T. Anastas, M. M. Kirchhoff, Acc. Chem. Res. 2002, 35, 686-694 and references cited therein.
3. W. Chen, W. Du, L. Yue, R. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Org. Biomol. Chem. 2007, 5, 816-821.
4. H. Doucet, M. Santelli, Synlett 2006, 13, 2001-2015.
5. J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651-2710.
6. The palladium cost was stated at 350 USD/Oz (9500 €/kg) on the New York market SE, 03/19/2007.
7. TON defined herein as the ratio [substrate on catalyst] multiplied by the yield of conversion in the desired product (i.e. 1 for a 100% yield), that corresponds to the value (mol product per mol catalyst).
8. V. Farina, Adv. Synth. Catal. 2004, 346, 1553-1582, this review provides an excellent overview of the challenges and advances related to the use of low loadings of catalyst.
9. A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. Int. Ed. 2000, 39, 4153-4155.
10. a) S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. Int. Ed. 2004, 43, 1871-1876;
11. b) T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685-4696.
12. See for instance: a) C. S. Consorti, G. Ebeling, F. R. Flores, F. Rominger, J. Dupont, Adv. Synth. Catal. 2004, 346, 617-624;
13. b) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687-11688.
14. See, for instance: a) D. A. Alonso, C. Nájera, M.-C. Pacheco, Org. Lett. 2000, 2, 1823-1826;
15. b) M. Ohff, A. Ohff, D. Milstein, Chem. Commun. 1999, 357-358;
16. c) H. Weissman, D. Milstein, Chem. Commun. 1999, 1901-1902.
17. R. B. Bedford, S. L. Hazelwood, M. E. Limmert, Chem. Commun. 2002, 2610-2611.
18. See, for instance: a) J. A. Loch, M. Albrecht, E. Peris, J. Mata, J. W. Faller, R. H. Crabtree, Organometallics 2002, 21, 700-706;
19. b) D. S. McGuinness, K. J. Cavell, Organometallics 2000, 19, 741-748.
20. D. Laurenti, M. Feuerstein, G. Pepe, H. Doucet, M. Santelli, J. Org. Chem. 2001, 66, 1633-1637.
21. W. A. Herrmann, C. Brossmer, K. Öfele, C.-P. Reisenger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848.
22. M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Brossmer, Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849.
23. D. A. Albisson, R. B. Bedford, S. E. Lawrence, P. Noelle Scully, Chem. Commun. 1998, 2095-2096.
24. D. A. Albisson, R. B. Bedford, P. Noelle Scully, Tetrahedron Lett. 1998, 39, 9793-9796.
25. J. P. Wolfe, S. L. Buchwald, Angew. Chem. Int. Ed. 1999, 38, 2413-2415.
26. J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550-9561.
27. a) Q. Shen, S. Shekhar, J. P. Stambuli, J. F. Hartwig, Angew. Chem. Int. Ed. 2005, 44, 1371-1375;
28. b) M. A. Fernández-Rodriguez, Q. Shen, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 2180-2181.
29. T. Hayashi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi, K. Hirotsu, J. Am. Chem. Soc. 1984, 106, 158-163.
30. For general reviews on high-efficiency catalysts in C-C and C-N cross-coupling reactions, see: a) A. Zapf, M. Beller, Chem. Commun. 2005, 431-440;
31. b) R. B. Bedford, C. S. J. Cazin, D. Holder, Coord. Chem. Rev. 2004, 248, 2283-2321.
32. U. Christmann, R. Vilar, Angew. Chem. Int. Ed. 2005, 44, 366-374 on monodentate bulky electron-rich phosphanes and carbenes for cross-coupling reactions.
33. a) J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527-2571;
34. b) I. P. Beletskaya, A. V. Cheprakov, J. Organomet. Chem. 2004, 689, 4055-4082 on palladacycle catalysis.
35. N. T. S. Phan, M. Van der Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609-679 on the nature of active species in Suzuki and Heck homogeneous catalysis.
36. a) H. Doucet, J.-C. Hierso, Angew. Chem. Int. Ed. 2007, 46, 834-871 on palladium homogeneous and heterogeneous catalysts in Heck-Sonogashira alkynylations;
37. b) R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874-922 for a review of the applications of the Sonogashira reaction.
38. th December 2000.
39. a) M. Feuerstein, D. Laurenti, H. Doucet, M. Santelli, Synthesis 2001, 2320-2326;
40. b) M. Feuerstein, D. Laurenti, C. Bougeant, H. Doucet, M. Santelli, Chem. Commun. 2001, 325-326.
41. M. Feuerstein, H. Doucet, M. Santelli, J. Org. Chem. 2001, 66, 5923-5925.
42. M. Feuerstein, F. Berthiol, H. Doucet, M. Santelli, Org. Biomol. Chem. 2003, 1, 2235-2237.
43. a) A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285-3288;
44. b) A. Alimardanov, L. Schmieder, A. H. M. de Vries, J. G. de Vries, Adv. Synth. Catal. 2004, 346, 1812-1817.
45. -4 mol-% (corresponding to maximum TONs of 1000000).
46. R. Broussier, E. Bentabet, R. Amardeil, P. Richard, P. Meunier, P. Kalck, B. Gautheron, J. Organomet. Chem. 2001, 637-639, 126-133.
47. A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 4176-4211.
48. J.-C. Hierso, A. Fihri, R. Amardeil, P. Meunier, H. Doucet, M. Santelli, B. Donnadieu, Organometallics 2003, 22, 4490-4499.
49. J.-C. Hierso, A. Fihri, V. V. Ivanov, B. Hanquet, N. Pirio, B. Donnadieu, B. Rebière, R. Amardeil, P. Meunier, J. Am. Chem. Soc. 2004, 126, 11077-11087.
50. 4·18] complexes isolated, the signals for nonbonded phosphorus atoms are found around -25 ppm, and around 40 ppm for Pd-bonded ones.
51. See A. Zapf, M. Beller, Chem. Eur. J. 2000, 6, 1830-1833 and references cited therein.
52. J.-C. Hierso, A. Fihri, R. Amardeil, P. Meunier, H. Doucet, M. Santelli, Tetrahedron 2005, 61, 9759-9766.
53. J.-C. Hierso, V. V. Ivanov, R. Amardeil, P. Richard, P. Meunier, Chem. Lett. 2004, 33, 1296-1297.
54. V. V. Ivanov, J.-C. Hierso, R. Amardeil, P. Meunier, Organometallics 2006, 25, 989-995.
55. J.-C. Hierso, A. Fihri, R. Amardeil, P. Meunier, H. Doucet, M. Santelli, V. V. Ivanov, Org. Lett. 2004, 6, 3473-3476.
56. A. Fihri, J.-C. Hierso, A. Vion, D. H. Nguyen, M. Urrutigoïty, P. Kalck, R. Amardeil, P. Meunier, Adv. Synth. Catal. 2005, 347, 1198-1202.
57. A. Fihri, J. Boudon, J.-C. Hierso, R. Amardeil, P. Meunier, P. Richard, Acta Crystallogr., Sect. E 2005, 61, 2267-2269.
58. D. H. Nguyen, M. Urrutigoïty, A. Fihri, J.-C. Hierso, P. Meunier, P. Kalck, Appl. Organomet. Chem. 2006, 20, 845-850.
59. A. Fihri, P. Meunier, J.-C. Hierso, Coord. Chem. Rev. 2007, doi:10.1016/j.ccr.2007.03.020.
60. For a review of multidentate ligands, see: J.-C. Hierso, R. Amardeil, E. Bentabet, R. Broussier, B. Gautheron, P. Meunier, P. Kalck, Coord. Chem. Rev. 2003, 236, 143-206.