Diametrically opposed carbenes on an α-cyclodextrin: Synthesis, characterization of organometallic complexes and Suzuki-Miyaura coupling in ethanol and in water

European Journal of Organic Chemistry

Volumn , Issue 18, 2013, Pages 3691-3699

  Guitet, Maxime ^a   Marcelo, Filipa ^b,c   De Beaumais, Ségolène Adam ^a   Zhang, Yongmin ^a   Jiménez Barbero, Jesús ^b   Tilloy, Sébastien ^d   Monflier, Eric ^d   Ménand, Mickaël ^a   Sollogoub, Matthieu ^a  

^a SORBONNE UNIVERSITÉ   (France)

^b CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

^c DEPARTAMENTO DE QUÍMICA   (Portugal)

^d UNIV LILLE   (France)

Author keywords

Carbene ligands; Cyclodextrins; Homogeneous catalysis; Nitrogen heterocycles; Palladium

Indexed keywords

EID: 84879217724     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201300190     Document Type: Article

References (82)

1. A. Igau, H. Grutzmacher, A. Baceiredo, G. Bertrand, J. Am. Chem. Soc. 1988, 110, 6463-6466.
2. A. J. Arduengo III, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361-363.
3. M. Poyatos, J. Á. Mata, E. Peris, Chem. Rev. 2009, 109, 3677-3707.
4. H. K. A. C. Coolen, P. W. N. M. van Leeuwen, R. J. M. Nolte, Angew. Chem. 1992, 104, 906;
5. Angew. Chem. Int. Ed. Engl. 1992, 31, 905-907.
6. S. Blanchard, L. Le Clainche, M.-N. Rager, B. Chansou, J.-P. Tuchagues, A. F. Duprat, Y. Le Mest, O. Reinaud, Angew. Chem. 1998, 110, 2861;
7. Angew. Chem. Int. Ed. 1998, 37, 2732-2735.
8. C. Wieser-Jeunesse, D. Matt, A. De Cian, Angew. Chem. 1998, 110, 3027;
9. Angew. Chem. Int. Ed. 1998, 37, 2861-2864.
10. B. Kersting, Angew. Chem. Int. Ed. 2001, 40, 3988-3990.
11. C. Gibson, J. Rebek Jr., Org. Lett. 2002, 4, 1887-1890.
12. D. Armspach, D. Matt, F. Peruch, P. Lutz, Eur. J. Inorg. Chem. 2003, 805-809.
13. A. Martinez, J.-P. Dutasta, J. Catal. 2009, 267, 188-192.
14. R. Gramage-Doria, D. Armspach, D. Matt, Coord. Chem. Rev. 2013, 257, 776-816, and references cited therein.
15. M. Frank, G. Maas, J. Schatz, Eur. J. Org. Chem. 2004, 607-613.
16. M. Frank, G. Maas, J. Schatz, Eur. J. Org. Chem. 2006, 2378-2383.
17. I. Dinarès, C. Garcia de Miguel, M. Font-Bardia, X. Solans, E. Alcalde, Organometallics 2007, 26, 5125-5128.
18. M. Sawamura, K. Kitayama, Y. Ito, Tetrahedron: Asymmetry 1993, 4, 1829-1832.
19. M. T. Reetz, J. Rudolph, Tetrahedron: Asymmetry 1993, 4, 2405-2406.
20. C. Yang, Y. K. Cheung, J. Yao, Y. T. Wong, G. Jia, Organometallics 2001, 20, 424-429.
21. M. T. Reetz, I. D. Kostas, S. R. Waldvogel, Inorg. Chem. Commun. 2002, 5, 252-254.
22. E. Engeldinger, L. Poorters, D. Armspach, D. Matt, L. Toupet, Chem. Commun. 2004, 634-635.
23. C. Machut-Binkowski, F. X. Legrand, N. Azaroual, S. Tilloy, E. Monflier, Chem. Eur. J. 2010, 16, 10195-10201.
24. F. X. Legrand, N. Six, C. Slomianny, H. Bricout, S. Tilloy, E. Monflier, Adv. Synth. Catal. 2011, 353, 1325-1334.
25. D. N. Tran, F. X. Legrand, S. Menuel, H. Bricout, S. Tilloy, E. Monflier, Chem. Commun. 2012, 48, 753-755.
26. D. Armspach, D. Matt, Chem. Commun. 1999, 1073-1074.
27. E. Engeldinger, D. Armspach, D. Matt, Angew. Chem. 2001, 113, 2594;
28. Angew. Chem. Int. Ed. 2001, 40, 2526-2529.
29. Y. T. Wong, C. Yang, K.-C. Ying, G. Ji, Organometallics 2002, 21, 1782-1787.
30. E. Engeldinger, D. Armspach, D. Matt, P. G. Jones, R. Welter, Angew. Chem. 2002, 114, 2705;
31. Angew. Chem. Int. Ed. 2002, 41, 2593-2596.
32. E. Engeldinger, D. Armspach, D. Matt, P. G. Jones, Chem. Eur. J. 2003, 9, 3091-3095.
33. L. Poorters, D. Armspach, D. Matt, L. Toupet, S. Choua, P. Turek, Chem. Eur. J. 2007, 13, 9448-9461.
34. S. Guieu, E. Zaborova, Y. Blériot, G. Poli, A. Jutand, D. Madec, G. Prestat, M. Sollogoub, Angew. Chem. 2010, 122, 2364;
35. Angew. Chem. Int. Ed. 2010, 49, 2314-2318.
36. L. Poorters, D. Armspach, D. Matt, L. Toupet, Eur. J. Org. Chem. 2003, 1377-1381.
37. L. Poorters, D. Armspach, D. Matt, L. Toupet, Dalton Trans. 2007, 3195-3202.
38. E. Zaborova, J. Deschamp, S. Guieu, Y. Blériot, G. Poli, M. Ménand, D. Madec, G. Prestat, M. Sollogoub, Chem. Commun. 2011, 47, 9206-9208.
39. F.-X. Legrand, M. Ménand, M. Sollogoub, S. Tilloy, E. Monflier, New J. Chem. 2011, 35, 2061-2065.
40. P. Mathew, A. Neels, M. Albrecht, J. Am. Chem. Soc. 2008, 130, 13534-13535.
41. G. Guisado-Barrios, J. Bouffard, B. Donnadieu, G. Bertrand, Angew. Chem. 2010, 122, 4869;
42. Angew. Chem. Int. Ed. 2010, 49, 4759-4762.
43. For selected references, see:, I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
44. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
45. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
46. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
47. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
48. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
49. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
50. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
51. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
52. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
53. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
54. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
55. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856.
56. D. Armspach, L. Poorters, D. Matt, B. Benmerad, F. Balegroune, L. Toupet, Org. Biomol. Chem. 2005, 3, 2588-2592.
57. T. Lecourt, A. J. Pearce, A. Herault, M. Sollogoub, P. Sinaÿ, Chem. Eur. J. 2004, 10, 2960-2971.
58. E. Zaborova, Y. Blériot, M. Sollogoub, Tetrahedron Lett. 2010, 51, 1254-1256.
59. S. Xiao, M. Yang, P. Sinaÿ, Y. Blériot, M. Sollogoub, Y. Zhang, Eur. J. Org. Chem. 2010, 1510-1516.
60. O. Bistri, P. Sinaÿ, M. Sollogoub, Tetrahedron Lett. 2005, 46, 7757-7760.
61. O. Bistri, P. Sinaÿ, M. Sollogoub, Chem. Commun. 2006, 1112-1114.
62. O. Bistri, P. Sinaÿ, M. Sollogoub, Tetrahedron Lett. 2006, 47, 4137-4139.
63. O. Bistri, P. Sinaÿ, J. Jiménez Barbero, M. Sollogoub, Chem. Eur. J. 2007, 13, 9757-9774.
64. S. Guieu, M. Sollogoub, Angew. Chem. 2008, 120, 7168;
65. Angew. Chem. Int. Ed. 2008, 47, 7060-7063.
66. S. Guieu, M. Sollogoub, J. Org. Chem. 2008, 73, 2819-2828.
67. E. Zaborova, M. Guitet, G. Prencipe, Y. Blériot, M. Ménand, M. Sollogoub, Angew. Chem. Int. Ed. 2013, 52, 639-644.
68. R. Breslow, J. B. Doherty, G. Guillot, C. Lipsey, J. Am. Chem. Soc. 1978, 100, 3227-3229.
69. E. Deunf, E. Zaborova, S. Guieu, Y. Blériot, J.-N. Verpeaux, O. Buriez, M. Sollogoub, C. Amatore, Eur. J. Inorg. Chem. 2010, 4720-4727.
70. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
71. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708;
72. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
73. C.-Y. Liao, K.-T. Chan, J.-Y. Zeng, C.-H. Hu, C.-Y. Tu, H. M. Lee, Organometallics 2007, 26, 1692-1702.
74. T. Nakamura, K. Ogata, S. Fukuzawa, Chem. Lett. 2010, 39, 920-922.
75. T. Hauch Fenger, J. Bjerre, M. Bols, ChemBioChem 2009, 10, 2492-2503.
76. T. Lecourt, J. M. Mallet, P. Sinaÿ, Carbohydr. Res. 2003, 338, 2417-2419.
77. B. Bertino-Ghera, F. Perret, B. Fenet, H. Parrot-Lopez, J. Org. Chem. 2008, 73, 7317-7326.
78. Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn, J. Am. Chem. Soc. 2003, 125, 3192-3193.
79. D. Matt, D. Armspach, Inorg. Chem. 2001, 40, 3505-3509.
80. S. Hanessian, A. Benalil, C. Laferrière, J. Org. Chem. 1995, 60, 4786-4797.
81. M. D. Hanwell, D. E. Curtis, D. C. Lonie, T. Vandermeersch, E. Zurek, G. R. Hutchison, J. Cheminform. 2012, 4;.
82. A. K. Rappe, C. J. Casewit, K. S. Colwell, W. A. Goddard, W. M. Skiff, J. Am. Chem. Soc. 1992, 114, 10024-10035. Ministério de Ciência e Tecnologia Competitividad