CuII-β-cyclodextrin complex as a nanocatalyst for the homo-and cross-coupling of arylboronic acids under ligand-and base-free conditions in air: Chemoselective cross-coupling of arylboronic acids in water

European Journal of Organic Chemistry

Volumn , Issue 33, 2011, Pages 6656-6662

  Kaboudin, Babak ^a   Abedi, Yaghoub ^a   Yokomatsu, Tsutomu ^b  

^a INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Chemoselectivity; Copper; Coupling; Cyclodextrins; Macrocyclic ligands

Indexed keywords

EID: 80855133473     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100994     Document Type: Article

References (83)

1. H. Yoshida, Y. Yamaryo, J. Ohshita, A. Kunai, Tetrahedron Lett. 2003, 44, 1541.
2. M. S. Wong, X. L. Zhang, Tetrahedron Lett. 2001, 42, 4087.
3. A. Lei, X. Zhang, Tetrahedron Lett. 2002, 43, 2525.
4. F. V. Singh, R. Vatsyayan, U. Roy, A. Goel, Bioorg. Med. Chem. Lett. 2006, 16, 2734.
5. H. Meier, Angew. Chem. 2005, 117, 2536;
6. Angew. Chem. Int. Ed. 2005, 44, 2482-2506.
7. G. Wu, H. F. Guo, K. Gao, Y. Liu, K. F. Bastow, S. L. Morris-Natschke, K. H. Lee, L. Xie, Bioorg. Med. Chem. Lett. 2008, 18, 5272.
8. R. A. Nelson Jr., J. A. Hope, G. M. Luedemann, L. E. McDaniel, C. P. Schaffner, J. Antibiot. 1986, 39, 335.
9. M. Ezkai, M. Iwami, M. Yamashita, S. Hashimoto, T. Komori, K. Umehara, Y. Mine, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1985, 38, 1453.
10. F. Ullmann, Ber. Dtsch. Chem. Ges. 1903, 36, 2389-2391.
11. F. Ullmann, Ber. Dtsch. Chem. Ges. 1904, 37, 853-857.
12. I. Goldberg, Ber. Dtsch. Chem. Ges. 1906, 39, 1691-1696.
13. Y. Miyake, M. Wu, M. J. Rahman, Y. Kuwatani, M. Iyoda, J. Org. Chem. 2006, 71, 6110.
14. X. Xu, D. Cheng, W. Pei, J. Org. Chem. 2006, 71, 6637.
15. Z. Xu, J. Mao, Y. Zhang, Catal. Commun. 2008, 9, 97.
16. G. Cahiez, A. Moyeux, J. Buendia, C. Duplais, J. Am. Chem. Soc. 2007, 129, 13788.
17. M. K. Robinson, V. S. Kochurina, J. M. Hanna, Tetrahedron Lett. 2007, 48, 7687.
18. N. Miyaura, A. Suzuki, Main Group Met. Chem. 1987, 10, 295-300.
19. D. J. Koza, E. Carita, Synthesis 2002, 2183-2186.
20. G. W. Kabalka, L. Wang, Tetrahedron Lett. 2002, 43, 3067-3068.
21. A. Suzuki, "Cross coupling reaction of organoboron compounds with organic halides" in Metal-catalysed Cross-coupling Reactions (Eds.:, F. Diederich, P. T. Stang), Wiley-VCH, Weinheim, 1998.
22. S. P. Stanforth, Tetrahedron 1998, 54, 263-303.
23. N. Kirai, Y. Yamamoto, Eur. J. Org. Chem. 2009, 1864-1867.
24. J. Mao, Q. Hua, G. Xie, Z. Yao, D. Shi, Eur. J. Org. Chem. 2009, 2262-2266.
25. F. V. Singh, H. A. Stefani, Tetrahedron Lett. 2010, 51, 863-867.
26. J. P. Parrish, Y. C. Jung, R. J. Floyd, K. W. Jung, Tetrahedron Lett. 2002, 43, 7899-7902.
27. L. M. Klingensmith, N. E. Leadbeater, Tetrahedron Lett. 2003, 44, 765-768.
28. Y. Yamamoto, R. Suzuki, K. Hattori, N. Nishiyama, Synlett 2006, 1027-1030.
29. C. Amatore, C. Cammoun, A. Jutand, Eur. J. Org. Chem. 2008, 4567-4570.
30. K. Mitsudo, T. Shiraga, H. Tanaka, Tetrahedron Lett. 2008, 49, 6593-6595.
31. A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168.
32. K. A. Smith, E. M. Campi, W. R. Jackson, S. Marcuccio, C. G. M. Naeslund, G. B. Deacon, Synlett 1997, 131-132.
33. A. W. Thomas, S. V. Ley, Angew. Chem. 2003, 115, 5558;
34. Angew. Chem. Int. Ed. 2003, 42, 5400-5449 and references cited therein
35. J.-B. Lan, G.-L. Zhang, X.-Q. Yu, J.-S. You, L. Chen, M. Yan, R.-G. Xie, Synlett 2004, 1095-1097.
36. M. L. Kantam, G. T. Venkanna, C. Sridhar, B. Sreedhar, B. M. Choudary, J. Org. Chem. 2006, 71, 9522-9524.
37. G. Cheng, M. Luo, Eur. J. Org. Chem. 2011, 2519-2523.
38. J. X. Qiao, P. Y. S. Lam, Synthesis 2011, 829.
39. A. S. Demir, O. Reis, M. Emrullahoglu, J. Org. Chem. 2003, 68, 10130-10134.
40. C. Gonzalez-Arellano, A. Corma, M. Iglesias, S. Sanchez, Chem. Commun. 2005, 1990-1992.
41. B. Kaboudin, T. Haruki, T. Yokomatsu, Synthesis 2011, 91-95.
42. K. Surendra, N. S. Krishnaveni, K. R. Rao, Chem. Commun. 2005, 669.
43. Y. Kang, L. Zhou, X. Li, J. Yuan, J. Mater. Chem. 2011, 21, 3704-3710.
44. B. H. Han, S. Polarz, M. Antonietti, Chem. Mater. 2001, 13, 3915-3919.
45. F. Hapitot, A. Ponchel, S. Tilloy, E. Monflier, C. R. Chim. 2011, 14, 149-166.
46. F. Hapiot, J. Lyskawa, H. Bricout, S. Tilloy, E. Monflier, Adv. Synth. Catal. 2004, 346, 83-89.
47. L. Strimbu, J. Liu, A. E. Kaifer, Langmuir 2003, 19, 483-485.
48. J. D. Senra, L. F. B. Malta, M. E. H. M. da Costa, R. C. Michel, L. C. S. Aguiar, A. B. C. Simas, O. A. C. Antunes, Adv. Synth. Catal. 2009, 351, 2411-2422.
49. A. Cassez, A. Ponchel, F. Hapiot, E. Monflier, Org. Lett. 2006, 8, 4823-4826.
50. E. Z. Messmer, Phys. Chem. 1927, 126, 369.
51. Y. Matsui, T. Kurita, Y. Date, Bull. Chem. Soc. Jpn. 1972, 45, 3229.
52. Y. Matsui, T. Kurita, M. Yagi, T. Okayama, K. Mochida, Y. Date, Bull. Chem. Soc. Jpn. 1975, 48, 2187.
53. K. Mochida, Y. Matsui, Chem. Lett. 1976, 963.
54. Y. Matsui, K. Kinugawa, Bull. CHem. Soc. Jpn. 1985, 58, 2981.
55. E. Norkus, G. Grinciene, T. Vuorinen, E. Butkus, R. Vaitukus, Supramol. Chem. 2003, 15, 425-431.
56. The mechanism of transmetallation of (hydroxido)metal complexes with arylboronic acids has been discussed, see: T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058.
57. T. Nishikawa, Y. Yamamoto, N. Miyaura, Organometallics 2004, 23, 4317-4324.
58. For a review, see:, T. Kauffmann, Angew. Chem. 1974, 86, 321-335;
59. Angew. Chem. Int. Ed. Engl. 1974, 13, 291-356.
60. for the dimetallic mechanism of copper salts for the homocoupling reactions, see:, G. Harada, M. Yoshida, M. Iyoda, Chem. Lett. 2000, 160-161.
61. Z. Rappoport, The Chemistry of Phenols, Wiley-VCH, Weinheim, 2003.
62. J. H. P. Tyman, Synthetic and Natural Phenols, Elsevier, New York, 1996.
63. R. Bal, M. Tada, T. Sasaki, Y. Iwasawa, Angew. Chem. 2006, 118, 462;
64. Angew. Chem. Int. Ed. 2006, 45, 448.
65. A. Tlili, N. Xia, F. Monnier, M. Taillefer, Angew. Chem. 2009, 121, 8881;
66. Angew. Chem. Int. Ed. 2009, 48, 8725-8728.
67. J. Xu, X. Wang, C. Shao, D. Su, G. Cheng, Y. Hu, Org. Lett. 2010, 12, 1964-1967.
68. Z. Rappoport, The Chemistry of Anilines, Wiley-Interscience, New York, 2003.
69. G. DAprano, M. Leclerc, G. Zotti, G. Schiavon, Chem. Mater. 1995, 7, 33-42.
70. F. Fache, E. Schulz, M. L. Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159-2231.
71. For example:, M. Nobis, B. Driessen-Holscher, Angew. Chem. 2001, 113, 4105;
72. Angew. Chem. Int. Ed. 2001, 40, 3983.
73. D. Hollmann, S. Bahn, A. Tillack, M. Beller, Angew. Chem. 2007, 119, 8440;
74. Angew. Chem. Int. Ed. 2007, 46, 8291.
75. G. Cami-Kobeci, J. M. J. Williams, Chem. Commun. 2004, 1072.
76. M. Larrosa, C. Guerrero, R. Rodriguez, J. Cruces, Synthesis 2010, 2101-2105.
77. D. M. T. Chan, K. L. Monaca, R.-P. Wanag, M. P. Winters, Tetrahedron Lett. 1998, 39, 2933-2936.
78. P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600-7601.
79. P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941-2944.
80. J. C. Antilla, S. L. Buchwald, Org. Lett. 2001, 3, 2077-2079.
81. G. C. H. Chiang, T. Olsson, Org. Lett. 2004, 6, 3079-3082.
82. J. P. Collman, M. Zhong, Org. Lett. 2000, 2, 1233-1236.
83. T. D. Quach, R. A. Batey, Org. Lett. 2003, 5, 4397-4400.