Eosin y catalyzed visible light mediated aerobic photo-oxidative cleavage of the C-C double bond of styrenes

Tetrahedron Letters

Volumn 56, Issue 5, 2015, Pages 653-656

  Singh, Atul K ^a   Chawla, Ruchi ^a   Yadav, Lal Dhar S ^a  

^a UNIVERSITY OF ALLAHABAD   (India)

Author keywords

Aldehydes; C C bond cleavage; Eosin Y; Photoredox catalysis; Styrenes; Visible light

Indexed keywords

ALDEHYDE; BENZOTHIAZOLINE DERIVATIVE; EOSIN; EOSIN Y; GLASS; PHOTOSENSITIZING AGENT; UNCLASSIFIED DRUG;

AIR; ARTICLE; CATALYSIS; CATALYST; CONTROLLED STUDY; COVALENT BOND; LIGHT; PHOTOOXIDATION; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 84920729299     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.11.141     Document Type: Article

References (65)

1. C.K. Prier, D.A. Rankic, and D.W.C. MacMillan Chem. Rev. 113 2013 5322
2. M. Majek, F. Filace, and J.A. von Wangelin Beilstein J. Org. Chem. 10 2014 981
3. D.P. Hari, and B. Konig Chem. Commun. 2014 6688
4. M.A. Ischay, M.S. Ament, and T.P. Yoon Chem. Sci. 3 2012 2807
5. R.A. Sheldon, and J.K. Kochi Metal Catalyzed Oxidations of Organic Compounds 1981 Academic Press New York
6. R. Stewart K. Wiberg, Oxidation in Organic Chemistry 1965 Academic Press New York
7. (c) M. Hudlicky Oxidations in Organic Chemistry American Chemical Society Monograph 186 1990 American Chemical Society Washington, DC
8. R.C. Larock Comprehensive Organic Transformations 2nd ed. 1999 Wiley-VCH New York 1234
9. D.G. Lee, and T. Chen B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 7 1991 Pergamon Press Oxford 541
10. A. Rajagopalan, M. Lara, and W. Kroutil Adv. Synth. Catal. 355 2013 3321
11. R. Criegee Angew. Chem., Int. Ed. Engl. 14 1975 745
12. P.S. Bailey Ozonation in Organic Chemistry 1978 Academic Press New York
13. C.E. Schiaffo, and P.H. Dussault J. Org. Chem. 73 2008 4688
14. M. O'Brien, I.R. Baxendale, and S.V. Ley Org. Lett. 12 2010 1596
15. R. Willand-Charnley, T.J. Fisher, B.M. Johnson, and P.H. Dussault Org. Lett. 14 2012 2242
16. R. Pappo, D.S. Allen, R.U. Lemieux Jr., and W.S. Johnson J. Org. Chem. 21 1956 478
17. Y. Qian, H. Nishino, and K. Kurosawa J. Heterocycl. Chem. 30 1993 209
18. X. Baucherel, J. Uziel, and S. Juge J. Org. Chem. 66 2001 4504
19. J.W. Boer, J. Brinksma, W.R. Browne, A. Meetsma, P.L. Alsters, R. Hage, and B.L. Feringa J. Am. Chem. Soc. 127 2005 7990
20. S.-T. Liu, V.K. Reddy, and R.-Y. Lai Tetrahedron 63 2007 1821
21. A.V. Biradar, B.R. Sathe, S.B. Umbarkar, and M.K. Dongare J. Mol. Catal. A: Chem. 285 2008 111
22. W.P. Griffith, A.G. Shoair, and M. Suriaatmaja Synth. Commun. 30 2000 3091
23. B. Plietker J. Org. Chem. 68 2003 7123
24. V. Kogan, M.M. Quintal, and R. Neumann Org. Lett. 7 2005 5039
25. K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, and A. Khorshidi Catal. Commun. 9 2007 416
26. A. Wang, and H. Jiang J. Org. Chem. 75 2010 2321
27. T.K.M. Shing, E.K.W.V. Tam, W.-F. Tai, I.H.F. Chung, and Q. Jiang Chem. Eur. J. 2 1996 50
28. N.M. Neisius, and B. Plietker J. Org. Chem. 73 2008 3218
29. D.H.R. Barton, and L. Wang Tetrahedron Lett. 35 1994 1519
30. H.R. Barton, and W. Chavasiri Tetrahedron 50 1994 19
31. A. Dhakshinamoorthy, and K. Pitchumani Tetrahedron 62 2006 9911
32. A. Dhakshinamoorthy, M. Alvaro, and H. Garcia ACS Catal. 1 2011 836
33. D. Xing, B. Guan, G. Cai, Z. Fang, L. Yang, and Z. Shi Org. Lett. 8 2006 693
34. B.R. Travis, R.S. Narayan, and B.J. Borhan J. Am. Chem. Soc. 124 2002 3824
35. A. Dhakshinamoorthy, and K. Pitchumani Catal. Commun. 10 2009 872
36. X. Wu, A.P. Davis, and A.J. Fry Org. Lett. 9 2007 5633
37. U.-St. Bauemer, and H.J. Schaefer J. Appl. Electrochem. 35 2005 1283
38. T. Wang, and N. Jiao J. Am. Chem. Soc. 135 2013 11692
39. R. Lin, F. Chen, and N. Jiao Org. Lett. 14 2012 4158
40. V. Narasimhan, R. Rathore, and S. Chandrasekaran Synth. Commun. 15 1985 769
41. F.V. Singh, H.M.S. Milagre, M.N. Eberlin, and H.A. Stefani Tetrahedron Lett. 50 2009 2312
42. K. Miyamoto, N. Tada, and M. Ochiai J. Am. Chem. Soc. 129 2007 2772
43. K. Miyamoto, Y. Sei, K. Yamaguchi, and M. Ochiai J. Am. Chem. Soc. 131 2009 1382
44. P.P. Thottumkara, and T.K. Vinod Org. Lett. 12 2010 5640
45. E.L. Clennan, and G.-L. Pan Org. Lett. 5 2003 4979
46. K. Gollnick, and A. Schnatterer Tetrahedron Lett. 25 1984 2735
47. S.-I. Hirashima, Y. Kudo, T. Nobuta, N. Tada, and A. Itoh Tetrahedron Lett. 50 2009 4328
48. L. Melone, C. Gambarotti, S. Prosperini, N. Pastori, F. Recupero, and C. Punta Adv. Synth. Catal. 353 2011 147
49. R. Lechner, S. Kummel, and B. Konig Photochem. Photobiol. Sci. 9 2010 1367
50. J. Eriksen, and C.S. Foote J. Am. Chem. Soc. 102 1980 6083
51. J. Eriksen, C.S. Foote, and T.L. Parker J. Am. Chem. Soc. 99 1977 6455
52. A.K. Singh, R. Chawla, A. Rai, and L.D.S. Yadav Chem. Commun. 2012 3766
53. R. Chawla, R. Kapoor, A.K. Singh, and L.D.S. Yadav Green Chem. 14 2012 1308
54. R. Chawla, A.K. Singh, and L.D.S. Yadav Tetrahedron 69 2013 1720
55. R. Chawla, A.K. Singh, and L.D.S. Yadav Synlett 2013 1558
56. A.K. Singh, R. Chawla, and L.D.S. Yadav Tetrahedron Lett. 54 2013 5099
57. A.K. Yadav, V.P. Srivastava, and L.D.S. Yadav New J. Chem. 37 2013 4119
58. T. Keshari, V.K. Yadav, V.P. Srivastava, and L.D.S. Yadav Green Chem. 16 2014 2986
59. V.P. Srivastava, A.K. Yadav, and L.D.S. Yadav Synlett 2014 665
60. A.K. Singh, R. Chawla, T. Keshari, V.K. Yadav, and L.D.S. Yadav Org. Biomol. Chem. 12 2014 8550
61. H. Chikashita, M. Miyazaki, and K. Itoh J. Chem. Soc., Perkin Trans. 1 1987 699
62. H. Chikashita, S. Nishida, M. Miyazaki, and K. Itoh Synth. Commun. 13 1983 1033
63. H. Chikashita, Y. Morita, and K. Itoh Synth. Commun. 15 1985 527
64. K. Saito, and T. Akiyama Chem. Commun. 2012 4573
65. C. Zhu, and T. Akiyama Org. Lett. 11 2009 4180