Self-buffering hybrid gold-polyoxometalate catalysts for the catalytic cyclization of acid-sensitive substrates

Chemistry - A European Journal

Volumn 18, Issue 41, 2012, Pages 12962-12965

  Dupré, Nathalie ^a   Brazel, Christian ^a   Fensterbank, Louis ^a   Malacria, Max ^a   Thorimbert, Serge ^a   Hasenknopf, Bernold ^a   Lacôte, Emmanuel ^a,b  

^a SORBONNE UNIVERSITÉ   (France)

^b INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

allenes; gold; organic inorganic hybrid composites; polyoxometalates; protonation

Indexed keywords

ALLENES; BENZYLIC ALCOHOLS; CATALYTIC CYCLIZATION; GOLD COMPLEXES; METAL OXIDE SURFACES; ORGANIC-INORGANIC HYBRID COMPOSITES; POLYOXOMETALATES; SELF-BUFFERING;

GOLD; HYDROCARBONS; OXIDES; PROTONATION;

GOLD COMPOUNDS;

EID: 84867068850     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201007     Document Type: Article

References (63)

1. A. Dolbecq, E. Dumas, C. R. Mayer, P. Mialane, Chem. Rev. 2010, 110, 6009
2. D.-L. Long, R. Tsunashima, L. Cronin, Angew. Chem. 2010, 122, 1780
3. Angew. Chem. Int. Ed. 2010, 49, 1736.
4. N. Mizuno, K. Yamaguchi, K. Kamata, Coord. Chem. Rev. 2005, 249, 1944
5. C. L. Hill, J. Mol. Catal. A 2007, 262, 1.
6. S. Luo, J. Li, H. Xu, L. Zhang, J.-P. Cheng, Org. Lett. 2007, 9, 3675
7. J. Li, S. Hu, S. Luo, J.-P. Cheng, Eur. J. Org. Chem. 2009, 132
8. C. Jahier, M. Cantuel, N. D. McClenaghan, T. Buffeteau, D. Cavagnat, F. Agbossou, M. Carraro, M. Bonchio, S. Nlate, Chem. Eur. J. 2009, 15, 8703
9. F. M. Toma, Nature Chem. 2010, 2, 826
10. M. Rostami, A. Khosropour, V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammadpoor-Baltork, Appl. Catal. A 2011, 397, 27
11. N. Mizuno, K. Yamaguchi, K. Kamata, Catal. Surv. Asia 2011, 15, 68.
12. I. Bar-Nahum, H. Cohen, R. Neumann, Inorg. Chem. 2003, 42, 3677
13. I. Bar-Nahum, R. Neumann, Chem. Commun. 2003, 2690
14. J. Ettedgui, R. Neumann, J. Am. Chem. Soc. 2009, 131, 4
15. D. Schaming, C. Allain, R. Farha, M. Goldmann, S. Lobstein, A. Giraudeau, B. Hasenknopf, L. Ruhlmann, Langmuir 2010, 26, 5101
16. J. Ettedgui, Y. Diskin-Posner, L. Weiner, R. Neumann, J. Am. Chem. Soc. 2011, 133, 188
17. J. Oble, B. Riflade, A. Noël, M. Malacria, S. Thorimbert, B. Hasenknopf, E. Lacôte, Org. Lett. 2011, 13, 5990.
18. W. Adam, P. L. Alsters, R. Neumann, C. R. Saha-Moeller, D. Seebach, A. K. Beck, R. Zhang, J. Org. Chem. 2003, 68, 8222
19. S. Berardi, M. Carraro, M. Iglesias, A. Sartorel, G. Scorrano, M. Albrecht, M. Bonchio, Chem. Eur. J. 2010, 16, 10662.
20. S. Borghèse, A. Blanc, P. Pale, B. Louis, Dalton Trans. 2011, 40, 1220
21. S. Borghèse, B. Louis, A. Blanc, P. Pale, Catal. Sci. Technol. 2011, 1, 981
22. M. Egi, M. Umemura, T. Kawai, S. Akai, Angew. Chem. 2011, 123, 12405
23. Angew. Chem. Int. Ed. 2011, 50, 12197
24. Y. Kikukawa, Y. Kuroda, K. Yamaguchi, N. Mizuno, Angew. Chem. 2012, 124, 2484
25. Angew. Chem. Int. Ed. 2012, 51, 2434.
26. B. Gockel, N. Krause, Org. Lett. 2006, 8, 4485
27. B. Gockel, N. Krause, Eur. J. Org. Chem. 2010, 311. For a similar reactivity in our group, see
28. R. Zriba, V. Gandon, C. Aubert, L. Fensterbank, M. Malacria, Chem. Eur. J. 2008, 14, 1482. For the latest reviews on gold chemistry, see
29. M. Rudolph, A. S. K. Hashmi, Chem. Soc. Rev. 2012, 41, 2448-2462
30. A. Corma, A. Leyva-Pérez, M. J. Sabater, Chem. Rev. 2011, 111, 1657
31. C. Aubert, L. Fensterbank, P. Garcia, M. Malacria, A. Simonneau, Chem. Rev. 2011, 111, 1954
32. N. Krause, C. Winter, Chem. Rev. 2011, 111, 1994.
33. P. Cordier, C. Aubert, M. Malacria, V. Gandon, E. Lacôte, Chem. Eur. J. 2010, 16, 9973
34. P. Cordier, C. Aubert, M. Malacria, E. Lacôte, V. Gandon, Angew. Chem. 2009, 121, 8913
35. Angew. Chem. Int. Ed. 2009, 48, 8757.
36. I. V. Kozhevnikov, "Heterogeneous Catalysis by Heteropoly Compounds" in Polyoxometalate Molecular Science Vol. 98 (Eds.: J. J. Borras-Almenar, E. Coronado, A. Müller, M. T. Pope), Kluwer, Dordrecht, 2003, p. 351
37. T. Ueda, H. Kotsuki, Heterocycles 2008, 76, 73
38. A. K. Ghosh, J. B. Moffat, J. Catal. 1986, 101, 238.
39. E. Mizushima, K. Sato, T. Hayashi, M. Tanaka, Angew. Chem. 2002, 114, 4745
40. Angew. Chem. Int. Ed. 2002, 41, 4563
41. E. Mizushima, T. Hayashi, M. Tanaka, Org. Lett. 2003, 5, 3349
42. H. Duan, S. Sengupta, J. L. Petersen, N. G. Akhmedov, X. Shi, J. Am. Chem. Soc. 2009, 131, 12100.
43. H. El Moll, B. Nohra, P. Mialane, J. Marrot, N. Dupré, B. Riflade, M. Malacria, S. Thorimbert, B. Hasenknopf, E. Lacôte, P. A. Aparicio, X. Lõpez, J. M. Poblet, A. Dolbecq, Chem. Eur. J. 2011, 17, 14129
44. C. Boglio, G. Lemière, B. Hasenknopf, S. Thorimbert, E. Lacôte, M. Malacria, Angew. Chem. 2006, 118, 3402
45. Angew. Chem. Int. Ed. 2006, 45, 3324.
46. M. Schulz-Dobrick, M. Jansen, Inorg. Chem. 2007, 46, 4380
47. K. Nomiya, T. Yoshida, Y. Sakai, A. Nanba, S. Tsuruta, Inorg. Chem. 2010, 49, 8247. For a different approach to golden POMs (polyoxoaurates), see
48. N. V. Izarova, N. Vankova, T. Heine, R. N. Biboum, B. Keita, L. Nadjo, U. Kortz, Angew. Chem. 2010, 122, 1930-1933
49. Angew. Chem. Int. Ed. 2010, 49, 1886-1889.
50. C. Boglio, K. Micoine, E. Derat, R. Thouvenot, B. Hasenknopf, S. Thorimbert, E. Lacôte, M. Malacria, J. Am. Chem. Soc. 2008, 130, 4553.
51. C. J. Besecker, V. W. Day, W. G. Klemperer, M. R. Thompson, J. Am. Chem. Soc. 1984, 106, 4125
52. K.-I. Shimizu, K. Miini, A. Satsuma, Catal. Commun. 2008, 9, 980
53. for a recent example of Lewis acid-base catalysis with POMs, see:, K. Suzuki, M. Sugawa, Y. Kikukawa, K. Kamata, K. Yamaguchi, N. Mizuno, Inorg. Chem. 2012, 51, 6953.
54. For evidence of the protodeauration as the rate-limiting step in the gold-catalyzed cyclization of alkynes, see:, W. Chaładaj, M. Corbet, A. Fürstner, Angew. Chem. 2012, 124, 7035
55. Angew. Chem. Int. Ed. 2012, 51, 6929.
56. S. Bareyt, S. Piligkos, B. Hasenknopf, P. Gouzerh, E. Lacôte, S. Thorimbert, M. Malacria, J. Am. Chem. Soc. 2005, 127, 6788.
57. N. Mézailles, L. Ricard, F. Gagosz, Org. Lett. 2005, 7, 4133
58. E. Herrero-Gõmez, C. Nieto-Oberhuber, S. Lõpez, J. Benet-Buchholz, A. E. Echavarren, Angew. Chem. 2006, 118, 5581
59. Angew. Chem. Int. Ed. 2006, 45, 5455
60. P. De Frémont, E. D. Stevens, M. R. Fructos, M. Mar Díaz-Requejo, P. J. Pérez, S. P. Nolan, Chem. Commun. 2006, 2045
61. V. Lavallo, G. D. Frey, S. Kousar, B. Donnadieu, G. Bertrand, Proc. Natl. Acad. Sci. USA 2007, 104, 13569
62. T. J. Brown, M. G. Dickens, R. A. Widenhoefer, J. Am. Chem. Soc. 2009, 131, 6350
63. N. D. Shapiro, F. D. Toste, Proc. Natl. Acad. Sci. USA 2008, 105, 2779.