Highly efficient synthesis of 9-fluorenones from 9H-fluorenes by air oxidation

Green Chemistry

Volumn 13, Issue 7, 2011, Pages 1891-1896

  Zhang, Xin ^a,b   Ji, Xuan ^a   Jiang, Shanshan ^a   Liu, Lili ^a   Weeks, Brandon L ^b   Zhang, Zhao ^a  

^a SHANXI UNIVERSITY   (China)

^b Texas Tech University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79960245352     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c1gc15136c     Document Type: Article

References (99)

1. A. A. Gouda Talanta 2009 80 151-157.
2. W.-Y. Wong G.-L. Lu K.-H. Choi Y.-H. Guo J. Organomet. Chem. 2005 690 177-186.
3. J. Wang M.-Q. Wu W.-B. Liu S.-W. Yang J.-W. Bai Q.-Q. Ding Y. Li Eur. Polym. J. 2010 46 1024-1031.
4. L. Oldridge M. Kastler K. Müllen Chem. Commun. 2006 885.
5. D. Cao Z. Liu Y. Deng G. Li G. Zhang Dyes Pigm. 2009 83 348-353.
6. E. W. Reinheimer J. R. Galán-Mascarós K. R. Dunbar Synth. Met. 2009 159 45-51.
7. A. Baheti P. Singh K. R. Justin Thomas Dyes Pigm. 2011 88 195-203.
8. S. Song D. Ju J. Li D. Li Y. Wei C. Dong P. Lin S. Shuang Talanta 2009 77 1707-1714.
9. X. Zeng C. Wang A. S. Batsanov M. R. Bryce J. Gigon B. Urasinska-Wojcik G. J. Ashwell J. Org. Chem. 2010 75 130-136.
10. X. Xu H. Zhang X. Liu Q. Zhuang Z. Han Eur. Polym. J. 2010 46 528-534.
11. Y. Lu M. Li Y. Zhang D. Hu L. Ke W. Xu Thermochim. Acta 2010 515 32-37.
12. N. Agarwal Dyes Pigm. 2009 83 328-333.
13. A. Farcas N. Jarroux V. Harabagiu P. Guégan Eur. Polym. J. 2009 45 795-803.
14. D. Hadjipavlou-Litina G. E. Magoulas M. Krokidis D. Papaioannou Eur. J. Med. Chem. 2010 45 298-310.
15. J. Kim Y. Jin S. Song S. H. Kim S. H. Park K. Lee H. Suh Macromolecules 2008 41 8324-8331.
16. K. Takagi S. Sugimoto M. Mitamura Y. Yuki S.-I. Matsuoka M. Suzuki Synth. Met. 2009 159 228-233.
17. K. Chupungars P. Rerngsamran S. Thaniyavarn Int. Biodeterior. Biodegrad. 2009 63 93-99.
18. Y. Lu Y. Zhou Y.-W. Quan Q.-M. Chen R.-F. Chen Z.-Y. Zhang Q.-L. Fan W. Huang J.-F. Ding Org. Lett. 2011 13 200-203.
19. M. E. El-Khouly Y. Chen X. Zhuang S. Fukuzumi J. Am. Chem. Soc. 2009 131 6370-6371.
20. X. Zhang J.-B. Han P.-F. Li X. Ji Z. Zhang Synth. Commun. 2009 39 3804-3815.
21. P. V. Ivchenko I. E. Nifant'ev V. A. Ezersky A. V. Churakov J. Organomet. Chem. 2011 696 1931-1934.
22. K. M. Omer S.-Y. Ku K.-T. Wong A. J. Bard J. Am. Chem. Soc. 2009 131 10733-10741.
23. Y. Wei S. Samori S. Tojo M. Fujitsuka J.-S. Lin C.-T. Chen T. Majima J. Am. Chem. Soc. 2009 131 6698-6707.
24. E. Kaya A. Balan D. Baran A. Cirpan L. Toppare Org. Electron. 2011 12 202-209.
25. K. M. Omer S.-Y. Ku Y.-C. Chen K.-T. Wong A. J. Bard J. Am. Chem. Soc. 2010 132 10944-10952.
26. H. S. Oh S. Liu H. Jee A. Baev M. T. Swihart P. N. Prasad J. Am. Chem. Soc. 2010 132 17346-17348.
27. Y.-M. Jeon J.-W. Kim C.-W. Lee M.-S. Gong Dyes Pigm. 2009 83 66-71.
28. J.-C. Tsai M. Kumar J.-G. Lin J. Hazard. Mater. 2009 164 847-855.
29. H. P. Rathnayake A. Cirpan F. E. Karasz M. Y. Odoi N. I. Hammer M. D. Barnes P. M. Lahti Chem. Mater. 2007 19 3265-3270.
30. N. Chidambaram S. Chandrasekaran J. Org. Chem. 1987 52 5048-5051.
31. R. Rangarajan E. J. Eisenbraun J. Org. Chem. 1985 50 2435-2438.
32. W.-F. Jiang H.-L. Wang A.-G. Wang Z.-Q. Li Synth. Commun. 2008 38 1888-1895.
33. R. Grisorio P. Mastrorilli G. Ciccarella G. P. Suranna C. F. Nobile Tetrahedron Lett. 2008 49 2078-2082.
34. J. G. Rodríguez J. L. Tejedor T. La Parra C. Díaz Tetrahedron 2006 62 3355-3361.
35. M. Nakanishi C. Bolm Adv. Synth. Catal. 2007 349 861-864.
36. S. Boitsov A. Riahi J. Muzart C. R. Acad. Sci., Ser. IIc: Chim. 2000 3 747-750.
37. X. Yang L. Zhou Y. Chen C. Chen Y. Su H. Miao J. Xu Catal. Commun. 2009 11 171-174.
38. S. Jana P. Wu T. Tatsumi J. Catal. 2006 240 268-274.
39. M. Nechab C. Einhorn J. Einhorn Chem. Commun. 2004 1500-1501.
40. K. Hashimoto H. Tanaka T. Ikeno T. Yamada Chem. Lett. 2002 31 582-583.
41. J.-Q. Wang L.-N. He New J. Chem. 2009 33 1637-1640.
42. M. Lukasiewicz D. Bogdal J. Pielichowski Adv. Synth. Catal. 2003 345 1269-1272.
43. Z. Lounis A. Riahi F. Djafri J. Muzart Appl. Catal., A 2006 309 270-272.
44. S. J. Singh R. V. Jayaram Catal. Commun. 2009 10 2004-2007.
45. P. Shejwalkar N. P. Rath E. B. Bauer Molecules 2010 15 2631-2650.
46. S.-J. Li Y.-G. Wang Tetrahedron Lett. 2005 46 8013-8015.
47. M. Lukasiewicz D. Bogdal J. Pielichowski Mol. Diversity 2006 10 491-493.
48. K. Kamata J. Kasai K. Yamaguchi N. Mizuno Org. Lett. 2004 6 3577-3580.
49. M. Juradogonzalez A. Sullivan J. Wilson Tetrahedron Lett. 2003 44 4283-4286.
50. A. Shaabani A. Rahmati M. Sharifi J. M. Rad B. Aghaaliakbari E. Farhangi D. G. Lee Monatsh. Chem. 2007 138 649-651.
51. A. Shaabani P. Mirzaei D. G. Lee Catal. Lett. 2004 97 119-123.
52. A. Shaabani P. Mirzaei S. Naderi D. G. Lee Tetrahedron 2004 60 11415-11420.
53. A. Shaabani D. G. Lee Tetrahedron Lett. 2001 42 5833-5836.
54. A. Shaabani A. Bazgir F. Teimouri D. G. Lee Tetrahedron Lett. 2002 43 5165-5167.
55. B. Bahramian F. D. Ardejani V. Mirkhani K. Badii Appl. Catal., A 2008 345 97-103.
56. V. Mirkhani M. Moghadam S. Tangestaninejad B. Bahramian Appl. Catal., A 2006 313 122-129.
57. B. Bahramian V. Mirkhani M. Moghadam S. Tangestaninejad Catal. Commun. 2006 7 289-296.
58. B. Bahramian V. Mirkhani S. Tangestaninejad M. Moghadam J. Mol. Catal. A: Chem. 2006 244 139-145.
59. V. Mirkhani M. Moghadam S. Tangestaninejad B. Bahramian Polyhedron 2006 25 2904-2914.
60. V. Mirkhani M. Moghadam S. Tangestaninejad H. Kargar Appl. Catal., A 2006 303 221-229.
61. M. Moghadam J. Mol. Catal. A: Chem. 2004 217 9-12.
62. S. Tangestaninejad M. Moghadam V. Mirkhani H. Kargar Ultrason. Sonochem. 2006 13 32-36.
63. S. M. Silvestre J. A. R. Salvador Tetrahedron 2007 63 2439-2445.
64. P. Marwah A. Marwah H. A. Lardy Green Chem. 2004 6 570-577.
65. C. Liu P. Zhao W. Huang Cent. Eur. J. Chem. 2007 5 303-315.
66. Y. Sprinzak J. Am. Chem. Soc. 1958 80 5449-5455.
67. L. Liu W.-Y. Wong Y.-W. Lam W.-Y. Tam Inorg. Chim. Acta 2007 360 109-121.
68. Y.-I. Park J.-H. Son J.-S. Kang S.-K. Kim J.-H. Lee J.-W. Park Chem. Commun. 2008 2143-2145.
69. R. W. Sinkeldam Y. Tor Org. Biomol. Chem. 2007 5 2523-2528.
70. J. Pei J. Ni X.-H. Zhou X.-Y. Cao Y.-H. Lai J. Org. Chem. 2002 67 4924-4936.
71. H. He B.-J. Pei A. W. M. Lee Green Chem. 2009 11 1857-1861.
72. T. Dohi N. Takenaga A. Goto H. Fujioka Y. Kita J. Org. Chem. 2008 73 7365-7368.
73. G. Yang Q. Zhang H. Miao X. Tong J. Xu Org. Lett. 2005 7 263-266.
74. A. Shaabani E. Farhangi A. Rahmati Appl. Catal., A 2008 338 14-19.
75. A. Shaabani E. Farhangi A. Rahmati Monatsh. Chem. 2008 139 905-908.
76. J.-R. Wang L. Liu Y.-F. Wang Y. Zhang W. Deng Q.-X. Guo Tetrahedron Lett. 2005 46 4647-4651.
77. H. Kawabata M. Hayashi Tetrahedron Lett. 2004 45 5457-5459.
78. R. G. Harvey E. Abu-Shqara C. X. Yang J. Org. Chem. 1992 57 6313-6317.
79. J. A. Mikroyannidis L.-R. Tsai Y. Chen Synth. Met. 2009 159 78-84.
80. H.-G. Li G. Wu M.-M. Shi H.-Z. Chen M. Wang Synth. Met. 2010 160 1648-1653.
81. Y. Song W. Xu D. Zhu Tetrahedron Lett. 2010 51 4894-4897.
82. R. Scaria K. Muellen J. Jacob Polymer 2010 51 5705-5711.
83. K. Esashika M. Yoshizawa-Fujita Y. Takeoka M. Rikukawa Synth. Met. 2009 159 2184-2187.
84. D.-H. Hwang J.-M. Kang J.-H. Eom M.-J. Park H.-J. Cho J.-I. Lee H.-Y. Chu C. Lee S.-H. Jin H.-K. Shim Curr. Appl. Phys. 2009 9 441-447.
85. Z. Q. Gao P. F. Xia P. K. Lo B. X. Mi H. L. Tam M. S. Wong K. W. Cheah C. H. Chen Org. Electron. 2009 10 666-673.
86. P. Sarrazin D. Beneventi D. Chaussy L. Vurth O. Stephan Colloids Surf., A 2009 334 80-86.
87. −1; the detection wavelength of 254 nm, the column temperature of 25 °C).
88. It is noteworthy that, in the procedure for the synthesis of 9-fluorenones, all crude products were washed with water for three times and then dried. So there is litte chance that any water soluble salts or base are incorporated to disturb the yields – this was also confirmed by a element analysis which was performed on all products.
89. Discharge standards of water pollutants for pharmaceutical industry chemical synthesis products category, GB 21904-2008.
90. W.-F. Jiang H.-L. Wang An-G. Wang Z.-Q Li Synth. Commun. 2008 38 1888-1895.
91. P. Sunanda S. Shubhankar K. R. Jayanta Tetrahedron Lett. 2010 51 5604-5608.
92. D. F. Detar D. I. Relyea J. Am. Chem. Soc. 1954 76 1680-1685.
93. C. W. Bennett W. G. Jewsbury J. P. Dupuis J. Am. Chem. Soc. 1946 68 2489-2490.
94. W. E. Hahn W. Cherasko Rocz. Chem. 1975 49 1309-1327.
95. H.-L Pan T. L. Fletcher J. Med. Chem. 1965 8 491-497.
96. J. H. Weisburger E. K. Weisburger H. P. Morris J. Am. Chem. Soc. 1952 74 4540-4543.
97. E. Campaigne Wm. B. Reid, Jr. J. Org. Chem. 1947 12 807-814.
98. I. M. Heilbron D. H. Hey R. Wilkinson J. Chem. Soc. 1938 113-116.
99. T. L. Fletcher M. J. Namkung W. H. Wetzel H. L. Pan J. Org. Chem. 1960 25 1342-1348.