Gold Nanoparticles Supported on a Layered Double Hydroxide as Efficient Catalysts for the One-Pot Synthesis of Flavones

Angewandte Chemie - International Edition

Volumn 54, Issue 45, 2015, Pages 13302-13306

  Yatabe, Takafumi ^a   Jin, Xiongjie ^a   Yamaguchi, Kazuya ^a   Mizuno, Noritaka ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

flavones; gold catalysis; heterogeneous catalysis; layered double hydroxides; one pot synthesis

Indexed keywords

CATALYSIS; FIBER OPTIC SENSORS; FLAVONOIDS; KETONES; METAL NANOPARTICLES; NANOPARTICLES; SYNTHESIS (CHEMICAL);

EFFICIENT CATALYSTS; FLAVONES; GOLD CATALYSIS; HYDROXYACETOPHENONES; LAYERED DOUBLE HYDROXIDES; MG-AL LAYERED DOUBLE HYDROXIDE; ONE-POT SYNTHESIS; STEP BY STEP PROCEDURE;

GOLD;

FLAVONE DERIVATIVE; GOLD; HYDROXIDE; HYDROXIDE ION; METAL NANOPARTICLE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CATALYSIS; FLAVONES; GOLD; HYDROXIDES; METAL NANOPARTICLES; MOLECULAR STRUCTURE;

EID: 84945491443     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201507134     Document Type: Article

References (76)

1. E. Middleton, Jr., C. Kandaswami, T. C. Theoharides, Pharmacol. Rev. 2000, 52, 673;
2. A. K. Verma, R. Pratap, Tetrahedron 2012, 68, 8523;
3. M. Singh, M. Kaur, O. Silakari, Eur. J. Med. Chem. 2014, 84, 206, and references therein.
4. J. Allan, R. Robinson, J. Chem. Soc. 1924, 125, 2192;
5. T. S. Wheeler, Org. Synth. 1952, 32, 72;
6. D. Nagarathnam, M. Cushman, Tetrahedron 1991, 47, 5071;
7. M. Kucukislamoglu, M. Nebioglu, M. Zengin, M. Arslan, N. Yayli, J. Chem. Res. 2005, 9, 556;
8. C. Jin, F. He, H. Wu, J. Chen, W. Su, J. Chem. Res. 2009, 1, 27.
9. T. Emilewicz, S. von Kostanecki, Ber. Dtsch. Chem. Ges. 1898, 31, 696;
10. H. S. Mahal, K. Venkataraman, J. Chem. Soc. 1936, 569;
11. W.-H. Huang, P.-Y. Chien, C.-H. Yang, A.-R. Lee, Chem. Pharm. Bull. 2003, 51, 339;
12. S. Alam, J. Chem. Sci. 2004, 116, 325;
13. P. D. Lokhande, S. S. Sakate, K. N. Taksande, B. Navghare, Tetrahedron Lett. 2005, 46, 1573;
14. N. Yao, A. Song, X. Wang, S. Dixon, K. S. Lam, J. Comb. Chem. 2007, 9, 668;
15. M. M. Naik, S. G. Tilve, V. B. Kamat, Tetrahedron Lett. 2014, 55, 3340;
16. Y. Hoshino, N. Takeno, Bull. Chem. Soc. Jpn. 1987, 60, 4468;
17. Y. K. Rao, S.-H. Fang, Y.-M. Tzeng, Bioorg. Med. Chem. 2005, 13, 6850;
18. H. S. Mahal, H. S. Rai, K. Venkataraman, J. Chem. Soc. 1935, 866;
19. Z. Du, H. Ng, K. Zhang, H. Zeng, J. Wang, Org. Biomol. Chem. 2011, 9, 6930.
20. For other synthetic procedures towards flavones, see:
21. Q. Yang, H. Alper, J. Org. Chem. 2010, 75, 948;
22. G. Maiti, R. Karmakar, R. N. Bhattacharya, U. Kayal, Tetrahedron Lett. 2011, 52, 5610;
23. M. Yoshida, Y. Fujino, K. Saito, T. Doi, Tetrahedron 2011, 67, 9993;
24. X.-F. Wu, H. Neumann, M. Beller, Chem. Eur. J. 2012, 18, 12595;
25. K. V. Sashidhara, M. Kumar, A. Kumar, Tetrahedron Lett. 2012, 53, 2355.
26. R. A. Sheldon, H. van Bekkum, Fine Chemicals through Heterogeneous Catalysis, Wiley-VCH, Weinheim, 2001;
27. Liquid Phase Oxidation via Heterogeneous Catalysis: Organic Synthesis and Industrial Applications (Eds.:, M. G. Clerici, O. A. Kholdeeva,), Wiley, Hoboken, 2013.
28. For excellent reviews on one-pot syntheses using heterogeneous catalysts, see:
29. M. J. Climent, A. Corma, S. Iborra, Chem. Rev. 2011, 111, 1072;
30. H. Miyamura, S. Kobayashi, Acc. Chem. Res. 2014, 47, 1054.
31. For the use of Au/LDH for aerobic alcohol oxidation, see:
32. T. Mitsudome, A. Noujima, T. Mizugaki, K. Jitsukawa, K. Kaneda, Adv. Synth. Catal. 2009, 351, 1890;
33. T. Mitsudome, A. Noujima, T. Mizugaki, K. Jitsukawa, K. Kaneda, Green Chem. 2009, 11, 793;
34. P. Liu, Y. Guan, R. A. van Santen, C. Li, E. J. M. Hensen, Chem. Commun. 2011, 47, 11540;
35. J. Feng, C. Ma, P. J. Miedziak, J. K. Edwards, G. L. Brett, D. Li, Y. Du, D. J. Morgan, G. J. Hutchings, Dalton Trans. 2013, 42, 14498;
36. S. Nishimura, Y. Yakita, M. Katayama, K. Higashimine, K. Ebitani, Catal. Sci. Technol. 2013, 3, 351;
37. J. Wang, X. Lang, B. Zhaorigetu, M. Jia, J. Wang, X. Guo, J. Zhao, ChemCatChem 2014, 6, 1737.
38. For selected examples of recently reported efficient functional-group transformations using supported gold catalysts and related reviews, see:
39. H. Sun, F.-Z. Su, J. Ni, Y. Cao, H.-Y. He, K.-N. Fan, Angew. Chem. Int. Ed. 2009, 48, 4390;
40. Angew. Chem. 2009, 121, 4454;
41. Y. Wang, D. Zhu, L. Tang, S. Wang, Z. Wang, Angew. Chem. Int. Ed. 2011, 50, 8917;
42. Angew. Chem. 2011, 123, 9079;
43. J.-F. Soulé, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2011, 133, 18550;
44. T. Mitsudome, K. Kaneda, Green Chem. 2013, 15, 2636;
45. K. Yamaguchi, Y. Wang, T. Oishi, Y. Kuroda, N. Mizuno, Angew. Chem. Int. Ed. 2013, 52, 5627;
46. Angew. Chem. 2013, 125, 5737;
47. K. Taniguchi, S. Itagaki, K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed. 2013, 52, 8420;
48. Angew. Chem. 2013, 125, 8578;
49. B. S. Takale, M. Bao, Y. Yamamoto, Org. Biomol. Chem. 2014, 12, 2005;
50. X. Liu, H.-Q. Li, S. Ye, Y.-M. Liu, H.-Y. He, Y. Cao, Angew. Chem. Int. Ed. 2014, 53, 7624;
51. Angew. Chem. 2014, 126, 7754;
52. A. Corma, A. Leyva-Rérez, M. J. Sabater, Chem. Rev. 2011, 111, 1657;
53. X. Liu, L. He, Y.-M. Liu, Y. Cao, Acc. Chem. Res. 2014, 47, 793, and references therein.
54. [7, 8] to the best of our knowledge, they have not been used for the oxidative dehydrogenation of saturated carbonyl compounds except for in our recent work; see:, X. Jin, K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed. 2014, 53, 455;
55. Angew. Chem. 2014, 126, 465.
56. Recently, several excellent oxidative dehydrogenation systems for saturated carbonyl compounds using palladium- or iridium-based homogeneous catalysts have been reported; see:
57. T. Diao, S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 14566;
58. Y. Izawa, D. Pun, S. S. Stahl, Science 2011, 333, 209;
59. Y. Moon, D. Kwon, S. Hong, Angew. Chem. Int. Ed. 2012, 51, 11333;
60. Angew. Chem. 2012, 124, 11495;
61. Y. Izawa, C. Zheng, S. S. Stahl, Angew. Chem. Int. Ed. 2013, 52, 3672;
62. Angew. Chem. 2013, 125, 3760;
63. T. Diao, T. J. Wadzinski, S. S. Stahl, Chem. Sci. 2012, 3, 887;
64. W. Gao, Z. He, Y. Qian, J. Zhao, Y. Huang, Chem. Sci. 2012, 3, 883;
65. A. N. Campbell, S. S. Stahl, Acc. Chem. Res. 2012, 45, 851;
66. T. Diao, D. Pun, S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 8205;
67. D. Pun, T. Diao, S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 8213;
68. S. Kusumoto, M. Akiyama, K. Nozaki, J. Am. Chem. Soc. 2013, 135, 18726;
69. N. Gigant, J.-E. Bäckvall, Chem. Eur. J. 2014, 20, 5890.
70. The detailed procedure for the preparation of Au/LDH is given in the Supporting Information. The gold content in Au/LDH was 2.4 wt %, and the average particle size of gold was 4.2 nm (standard deviation, σ=1.2 nm; Figure S4).
71. F. Cavani, F. Trifirò, A. Vaccari, Catal. Today 1991, 11, 173;
72. M. J. Climent, A. Corma, S. Iborra, J. Primo, J. Catal. 1995, 151, 60;
73. B. M. Choudary, M. L. Kantam, C. R. V. Reddy, K. K. Rao, F. Figueras, J. Mol. Catal. A 1999, 146, 279;
74. K. Kaneda, K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani, Catal. Surv. Jpn. 2000, 4, 31.
75. R. A. Sheldon, M. Wallau, I. W. C. E. Arends, U. Schuchardt, Acc. Chem. Res. 1998, 31, 485.
76. M. Conte, H. Miyamura, S. Kobayashi, V. Chechik, J. Am. Chem. Soc. 2009, 131, 7189.