Ligand- and base-free synthesis of phenols by rapid oxidation of arylboronic acids using iron(III) oxide

Tetrahedron Letters

Volumn 55, Issue 4, 2014, Pages 811-814

  Sawant, Sanghapal D ^a,b   Hudwekar, Abhinandan D ^a,b   Aravinda Kumar, K A ^a   Venkateswarlu, Vunnam ^a,b   Singh, Parvinder Pal ^a,b   Vishwakarma, Ram A ^a,b  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

^b ACADEMY OF SCIENTIFIC AND INNOVATIVE RESEARCH ACSIR   (India)

Author keywords

Fe2O3 photocatalyst; Arylboronic acid; Oxidation; Phenol; Solar VIS light irradiation

Indexed keywords

ARYLBORONIC ACID; BORONIC ACID DERIVATIVE; IRON OXIDE; OXYGEN; PHENOL DERIVATIVE; UNCLASSIFIED DRUG; ATMOSPHERIC OXYGEN; LIGAND;

ARTICLE; CATALYST; CHEMICAL REACTION; LIGHT; OXIDATION; PHOTOCATALYSIS; SOLAR RADIATION; SYNTHESIS; ADSORPTION; DISSOLUTION; IRRADIATION; MASS FRAGMENTOGRAPHY; OXIDATION REDUCTION REACTION;

EID: 84892431822     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.12.003     Document Type: Article

References (44)

1. P. Hanson, J.R. Jones, A.B. Taylor, P.H. Walton, and A.W. Timms J. Chem. Soc., Perkin Trans. 2 2002 1135 1150
2. T. George, R. Mabon, G. Sweeney, J.B. Sweeney, and A. Tavassoli J. Chem. Soc., Perkin Trans. 1 2000 2529 2574
3. J.B. Sweeney Contemp. Org. Synth. 4 1997 435 453
4. For more recent innovative approaches, see: C. Hoarau, and T.R.R. Pettus Synlett 2003 127 137
5. Z. Guo, A.G. Schultz, and E.G. Antoulinakis Org. Lett. 3 2001 1177 1180
6. I. Marchueta, S. Olivella, L. Sola, A. Moyano, M.A. Pericas, and A. Riera Org. Lett. 3 2001 3197 3200
7. S. Serra, C. Fuganti, and A. Moro J. Org. Chem. 66 2001 7883 7888
8. A.S.K. Hashmi, T.M. Frost, and J.W. Bats J. Am. Chem. Soc. 122 2000 11553 11554
9. V. Gevorgyan, and Y. Yamamoto J. Organomet. Chem. 576 1999 232 247
10. J.H.P. Tyman Synthetic and Natural Phenols 1996 Elsevier New York
11. C. Hoarau, and T.R.R. Pettus Synlett 2003 127
12. P. Hanson, J.R. Jones, A.B. Taylor, P.H. Walton, and A.W. Timms J. Chem. Soc., Perkin Trans. 2 2002 1135
13. T. George, R. Mabon, G. Sweeney, B.J. Sweeney, and A. Tavassoli J. Chem. Soc., Perkin Trans. 1 2000 2529 and reference cited therein
14. K.G. Thakur, and G. Sekar Chem. Commun. 2011 6692
15. A. Mehmood, and N.E. Leadbeater Catal. Commun. 12 2010 64
16. P.P. Singh, S. Gudup, S. Ambala, U. Singh, S. Dadhwal, B. Singh, S.D. Sawant, and R.A. Vishwakarma Chem. Commun. 2011 5852 5854
17. P.P. Singh, S. Gudup, H. Aruri, U. Singh, S. Ambala, M. Yadav, S.D. Sawant, and R.A. Vishwakarma Org. Biomol. Chem. 10 2012 1587 1597
18. A.L. Linsebigler, G. Lu, and J.T. Yates Jr. Chem. Rev. 95 1995 735 758
19. D.F. Ollis, and H. Al-Ekabi Photocatalytic Purification and Treatment of Water and Air 1993 Elsevier New York
20. Z.Y. Zhang, and P.A. Maggard J. Photochem. Photobiol., A 8 2007 186
21. Y. Takahara, J.N. Kondo, T. Takata, D. Lu, and K. Domen Chem. Mater. 13 2001 1994
22. B.C. Faust, M.R. Hoffmann, and D.W. Bahnemann J. Phys. Chem. 93 1989 6371 6381
23. B.C. Faust, and M.R. Hoffmann Environ. Sci. Technol. 20 1986 943 948
24. H. Fu, X. Quan, Z. Liu, and S. Chen Langmuir 20 2004 4867 4873
25. M. Chirita, and I. Grozescu Chem. Bull. Politech. Univ. (Timisoara) 54 2009 1
26. A.B. Isaev, Z.M. Aliev, N.K. Adamadzieva, N.A. Alieva, and G.A. Magomedova Nanotechnologies in Russia 4 2009 475 479
27. C. Zhu, R. Wang, and J.R. Falck Org. Lett. 14 2012 3494 3497
28. H.C. Brown, M.M. Midland, and G.W. Kabalka J. Am. Chem. Soc. 93 1971 1024 1025
29. G.W. Kabalka, R.M. Lambrecht, M. Sajjad, J.S. Fowler, S.A. Kunda, G.W. McCollum, and R. MacGregor Int. J. Appl. Radiat. Isot. 35 1985 853
30. E. Kianmehr, M. Yahyaee, and K. Tabatabai Tetrahedron Lett. 48 2007 2713 2715
31. A.N. Cammidge, V.H.M. Goddard, C.P.J. Schubert, H. Gopee, D.L. Hughes, and D. Gonzalez-Lucas Org. Lett. 13 2011 6034 6037
32. J. Xu, X. Wang, C. Shao, D. Su, G. Cheng, and Y. Hu Org. Lett. 12 2010 1964
33. H. Yang, Y. Li, M. Jiang, J. Wang, and H. Fu Chem. Eur. J. 17 2011 5652
34. K. Inamoto, K. Nozawa, M. Yonemoto, and Y. Kondo Chem. Commun. 2011 11775
35. B. Kaboudin, Y. Abedi, and T. Yokomatsu Eur. J. Org. Chem. 33 2011 6656
36. A.D. Chowdhury, S.M. Mobin, S. Mukherjee, S. Bhaduri, and G.K. Lahiri Eur. J. Inorg. Chem. 21 2011 3232
37. K.S. Webb, and D. Levy Tetrahedron Lett. 36 1995 5117
38. J. Simon, S. Salzbrunn, G.K.S. Prakash, N.A. Petasis, and G.A. Olah J. Org. Chem. 66 2001 633
39. B.R. Travis, B.P. Ciaramitaro, and B. Borhan Eur. J. Org. Chem. 20 2002 3429
40. G.K.S. Prakash, S. Chacko, C. Panja, T.E. Thomas, L. Gurung, G. Rasul, T. Mathew, and G.A. Olah Adv. Synth. Catal. 351 2009 1567
41. A. Gogoi, and U. Bora Synlett 2012 1079 1081
42. A. Gogoi, and U. Bora Tetrahedron Lett. 54 2013 1821 1823
43. N. Mulakayala, Ismail, M.K. Kottur, R.K. Rapolu, B. Kandagatla, P. Rao, S. Oruganti, and M. Pal Tetrahedron Lett. 53 2012 6004 6007
44. S.P. Pitre, C.D. McTiernan, H. Ismaili, and J.C. Scaiano J. Am. Chem. Soc. 135 2013 13286 13289