Chemoselective aerobic photo-oxidation of 9H-fluorenes for the synthesis of 9-fluorenones

Tetrahedron Letters

Volumn 55, Issue 34, 2014, Pages 4736-4738

  Kojima, Masahiro ^a   Oisaki, Kounosuke ^a   Kanai, Motomu ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

9 Fluorenone; Aerobic oxidation; Chemoselectivity; Copper; Photoreaction

Indexed keywords

CUPROUS ION; FLUORENE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYST; DRUG SELECTIVITY; IRRADIATION; OXIDATION; PH; PHOTOOXIDATION; PHOTOREACTIVITY; REACTION ANALYSIS; ROOM TEMPERATURE; SYNTHESIS;

EID: 84906082483     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.06.038     Document Type: Article

References (54)

1. R.F. Krueger, and G.D. Mayer Science 169 1970 1213 1214
2. P. Chandra, G. Will, D. Gericke, and A. Gotz Biochem. Pharmacol. 23 1974 3259 3265
3. P.J. Perry, M.A. Read, R.T. Davies, S.M. Gowan, A.P. Reszka, A.A. Wood, L.R. Kelland, and S. Neidle J. Med. Chem. 42 1999 2679 2684
4. X. Zhang, J.-K. Xu, J. Wang, N.-L. Wang, H. Kurihara, S. Kitanaka, and X.-S. Yao J. Nat. Prod. 70 2007 24 28
5. D. Chen, M. Misra, L. Sower, J.W. Peterson, G.E. Kellogg, and C.H. Schein Bioorg. Med. Chem. 16 2008 7225 7233
6. C.A. Briggs, M.R. Schrimpf, D.J. Anderson, E.J. Gubbins, J.H. Gronlien, M. Hakerud, H. Ween, K. Thorin-Hagene, J. Malysz, J. Li, W.H. Bunnelle, M. Gopalakrishnan, and M.D. Meyer Br. J. Pharmacol. 153 2008 1054 1061
7. F. Uckert, Y.H. Tak, K. Müllen, and H. Basser Adv. Mater. 12 2000 905 908
8. S. Panozzo, J.C. Vial, Y. Kervella, and O. Stephan J. Appl. Phys. 92 2002 3495 3502
9. A.P. Kulkarni, X.X. Kong, and S.A. Jenekhe J. Phys. Chem. B 108 2004 8689 8701
10. L. Oldridge, M. Kastler, and K. Müllen Chem. Commun. 2006 885 887
11. G.L. Eakins, J.S. Alford, B.J. Tiegs, B.E. Breyfogle, and C.J. Stearman J. Phys. Org. Chem. 24 2011 1119 1128
12. L.A. Estrada, J.E. Yarnell, and D.C. Neckers J. Phys. Chem. A 115 2011 6366 6375
13. B.D. Rose, D.T. Chase, C.D. Weber, L.N. Zakharov, M.C. Lonergan, and M.M. Haley Org. Lett. 13 2011 2106 2109
14. C.J. Qin, A. Islam, and L.Y. Han J. Mater. Chem. 22 2012 19236 19243
15. Recent examples: A. Shaabani, P. Mirzaei, S. Naderi, and D.G. Lee Tetrahedron 60 2004 11415 11420
16. J.R. Wu, Y. Chen, and T.Y. Wu J. Appl. Polym. Sci. 119 2011 2576 2583
17. Y. Sarrafi, M. Tajbakhsh, R. Hosseinzadeh, M. Sadatshahabi, and K. Alimohammadi Synth. Commun. 42 2012 678 685
18. T. Dohi, N. Takenaga, A. Goto, H. Fujioka, and Y. Kita J. Org. Chem. 73 2008 7365 7368
19. M. Catir, and H. Kilic Synlett 2010 1319 1322
20. V.N. Telvekar, and K.A. Sasane Synth. Commun. 42 2012 1325 1329
21. S. Murahashi, Y. Oda, T. Naota, and T. Kuwabara Tetrahedron Lett. 34 1993 1299 1302
22. M. Nakanishi, and C. Bolm Adv. Synth. Catal. 349 2007 861 864
23. T. Nagano, and S. Kobayashi Chem. Lett. 37 2008 1042 1043
24. H. Li, Z. Li, and Z. Shi Tetrahedron 65 2009 1856 1858
25. J. Zhang, Z. Wang, Y. Wang, C. Wan, X. Zheng, and Z. Wang Green Chem. 11 2009 1973 1978
26. L.-Q. Cui, K. Liu, and C. Zhang Org. Biomol. Chem. 9 2011 2258 2265
27. H. Peng, A. Lin, Y. Zhang, H. Jiang, J. Zhou, Y. Cheng, C. Zhu, and H. Hu ACS Catal. 2 2012 163 167
28. A.S. Burange, S.R. Kale, and R.V. Jayaram Tetrahedron Lett. 53 2012 2989 2992
29. Y. Gao, G. Hu, J. Zhong, Z. Shi, Y. Zhu, D.S. Su, J. Wang, X. Bao, and D. Ma Angew. Chem., Int. Ed. 52 2013 2109 2113
30. J. Hong, K.E. Djernes, I. Lee, R.J. Hooley, and F. Zaera ACS Catal. 3 2013 2154 2157
31. Y. Xu, Z. Yang, J. Hu, and J. Yan Synthesis 45 2013 370 374
32. Y. Ishii, K. Nakayama, M. Takeno, S. Sakaguchi, T. Iwahama, and Y. Nishiyama J. Org. Chem. 60 1995 3934 3935
33. M. Nechab, C. Einhorn, and J. Einhorn Chem. Commun. 2004 1500 1501
34. K. Kamata, J. Kasai, K. Yamaguchi, and N. Mizuno Org. Lett. 6 2004 3577 3580
35. H. Kawabata, and M. Hayashi Tetrahedron Lett. 45 2004 5457 5459
36. G.Y. Yang, Q.H. Zhang, H. Miao, X.L. Tong, and J. Xu Org. Lett. 7 2005 263 266
37. A. Shaabani, E. Farhangi, and A. Rahmati Appl. Catal., A 338 2008 14 19
38. G. Zheng, C. Liu, Q. Wang, M. Wang, and G. Yang Adv. Synth. Catal. 351 2009 2638 2642
39. G. Urgoitia, R. SanMartin, M. Teresa Herrero, and E. Dominguez Green Chem. 13 2011 2161 2166
40. R.G. Harvey, E. Abushqara, and C.X. Yang J. Org. Chem. 57 1992 6313 6317
41. (b) Walters, M. E.; Kolonko, R. P.; Wehmeyer R. M. U.S. Patent 9,607,694, 1997
42. K.K. Park, L.K. Tsou, and A.D. Hamilton Synthesis 2006 3617 3620
43. G. Pozzi, S. Quici, and R.H. Fish Adv. Synth. Catal. 350 2008 2425 2436
44. X. Zhang, X. Ji, S. Jiang, L. Liu, B.L. Weeks, and Z. Zhang Green Chem. 13 2011 1891 1896
45. Recent reviews of the photocatalyst in organic synthesis: K. Zeitler Angew. Chem., Int. Ed. 48 2009 9785 9789
46. T.P. Yoon, M.A. Ischay, and J. Du Nat. Chem. 2 2010 527 532
47. J. Xuan, and W.-J. Xiao Angew. Chem., Int. Ed. 51 2012 6828 6838
48. L. Shi, and W. Xia Chem. Soc. Rev. 41 2012 7687 7697
49. J.W. Tucker, and C.R.J. Stephenson J. Org. Chem. 77 2012 1617 1622
50. N. Hoffmann ChemSusChem 5 2012 352 371
51. C.K. Prier, D.A. Rankic, and D.W.C. MacMillan Chem. Rev. 113 2013 5322 5363
52. J. Xie, H. Jin, P. Xu, and C. Zhu Tetrahedron Lett. 55 2014 36 48
53. I.N. Lykakis, and M. Orfanopoulos Tetrahedron Lett. 45 2004 7645 7649
54. J. Rosenthal, T.D. Luckett, J.M. Hodgkiss, and D.G. Nocera J. Am. Chem. Soc. 128 2006 6546 6547