Cu(II)-catalyzed oxidative esterification of 2-carbonyl substituted phenols from the alcohol oxidation level

Tetrahedron

Volumn 69, Issue 45, 2013, Pages 9391-9397

  Sharma, Satyasheel ^a   Park, Jihye ^a   Kim, Mirim ^a   Kwak, Jong Hwan ^a   Jung, Young Hoon ^a   Kim, In Su ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

Alcohols; Aryl benzoate; Copper; Esterification; Phenols

Indexed keywords

ALCOHOL; BENZOIC ACID DERIVATIVE; CARBONYL DERIVATIVE; CUPRIC ION; OXIDIZING AGENT; PHENOL DERIVATIVE; SOLVENT;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; ESTERIFICATION; OXIDATION; OXIDATIVE ESTERIFICATION; PRIORITY JOURNAL; REACTION OPTIMIZATION; SOLVENT EFFECT; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84884675591     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.08.079     Document Type: Article

References (52)

1. J. Otera Esterification: Methods, Reaction and Application 2nd ed. 2010 Wiley-VCH Weinheim, Germany
2. R.C. Larock Comprehensive Organic Transformations: A Guide to Functional Group Preparations 2nd ed. 1999 Wiley-VCH New York, NY
3. W. Riemenschneider, H.M. Bolt, and Esters Organic in Ullmann's Encyclopedia of Industrial Chemistry 2005 Wiley-VCH Weinheim, Germany
4. D.V. Rosato, and M.V. Rosato Plastic Product Material and Process Selection Handbook 2004 Elsevier New York, NY
5. J.S. Carey, D. Laffan, C. Thomson, and M.T. Williams Org. Biomol. Chem. 4 2006 2337
6. R.W. Dugger, J.A. Ragan, and D.H.B. Ripin Org. Process Res. Dev. 9 2005 253
7. K. Ekoue-Kovi, and C. Wolf Chem. - Eur. J. 14 2008 6302
8. W.-J. Yoo, and C.-J. Li Tetrahedron Lett. 48 2007 1033
9. B. Xu, X. Liu, J. Haubrich, and C.M. Friend Nat. Chem. 2 2010 61
10. X.-F. Wu, and C. Darcel Eur. J. Org. Chem. 2009 1144
11. B.E. Maki, and K.A. Scheidt Org. Lett. 10 2008 4331
12. N.T. Reynolds, J. Read de Alaniz, and T. Rovis J. Am. Chem. Soc. 126 2004 9518
13. N.T. Reynolds, and T. Rovis J. Am. Chem. Soc. 127 2005 16406
14. M. He, G.J. Uc, and J.W. Bode J. Am. Chem. Soc. 128 2006 15088
15. S. Kiyooka, Y. Wada, M. Ueno, T. Yokoyama, and R. Yokoyama Tetrahedron 63 2007 12695
16. B.R. Travis, M. Sivakumar, G.O. Hollist, and B. Borhan Org. Lett. 5 2003 1031
17. G. Dobereiner, and R. Crabtree Chem. Rev. 110 2010 681
18. G. Guillena, D. Ramón, and M. Yus Angew. Chem., Int. Ed. 46 2007 2358
19. G. Tojo, and M. Fernández Oxidation of Alcohols to Aldehydes and Ketones 2006 Springer Berlin, Germany
20. J.F. Bower, I.S. Kim, R.L. Patman, and M.J. Krische Angew. Chem., Int. Ed. 48 2009 34
21. B.E. Maki, A. Chan, E.M. Phillips, and K.A. Scheidt Org. Lett. 9 2007 371
22. B.E. Maki, A. Chan, E.M. Phillips, and K.A. Scheidt Tetrahedron 65 2009 3102
23. C. Liu, J. Wang, L. Meng, Y. Deng, Y. Li, and A. Lei Angew. Chem., Int. Ed. 50 2011 5144
24. S. Gowrisankar, H. Neumann, and M. Beller Angew. Chem., Int. Ed. 50 2011 5139
25. A. Moretto, A. Nicolli, and M. Lotti Toxicol. Appl. Pharmacol. 219 2007 196
26. M.C. Berndt, M.R. Bowles, G.J. King, and B. Zerner Biochim. Biophys. Acta 1298 1996 159
27. M.D. Barratt, D.A. Basketter, and D.W. Roberts Toxicol. in Vitro 8 1994 823
28. J.J. Child, T. Oka, F.J. Simpson, and H.G. Krishnamurty Can. J. Microbiol. 17 1971 1455
29. M.H. Sarvari, and H. Sharghi Tetrahedron 61 2005 10903
30. F. Tamaddon, M.A. Amrollahi, and L. Sharafat Tetrahedron Lett. 46 2005 7841
31. S.T.A. Shah, K.M. Khan, H. Hussain, M.U. Anwar, M. Fecker, and W. Voelter Tetrahedron 61 2005 6652
32. Y. Oohashi, K. Fukumoto, and T. Mukaiyama Bull. Chem. Soc. Jpn. 78 2005 1508
33. G.A. Olah, Q. Wang, N.J. Trivedi, and G.K.S. Prakash Synthesis 1991 739
34. J.S. Yadav, B.V.S. Reddy, A.K. Basak, and A.V. Narsaiah Chem. Lett. 33 2004 248
35. H. Kotsuki, K. Arimura, T. Araki, and T. Shinohara Synlett 1999 462
36. F. Toda, M. Yagi, and K. Kiyoshige J. Chem. Soc., Chem. Commun. 1988 958
37. F. Luo, C. Pan, J. Cheng, and F. Chen Tetrahedron 67 2011 5878
38. D. Zhang, and C. Pan Catal. Commun. 20 2012 41
39. A. Fougerousse, E. Gonzalez, and R. Brouillard J. Org. Chem. 65 2000 583
40. A. Furstner, and D.N. Jumban Tetrahedron 48 1992 5991
41. J. Park, E. Park, A. Kim, Y. Lee, K.-W. Chi, J.H. Kwak, Y.H. Jung, and I.S. Kim Org. Lett. 13 2011 4390
42. S. Sharma, E. Park, J. Park, and I.S. Kim Org. Lett. 14 2012 906
43. S. Sharma, J. Park, E. Park, A. Kim, M. Kim, J.H. Kwak, Y.H. Jung, and I.S. Kim Adv. Synth. Catal. 355 2013 332
44. J. Park, A. Kim, S. Sharma, M. Kim, E. Park, Y. Jeon, Y. Lee, J.H. Kwak, Y.H. Jung, and I.S. Kim Org. Biomol. Chem. 11 2013 2766
45. A.J. Catino, J.M. Nichols, H. Choi, S. Gottipamula, and M.P. Doyle Org. Lett. 7 2005 5167
46. E.C. McLaughlin, H. Choi, K. Wang, G. Chiou, and M.P. Doyle J. Org. Chem. 74 2009 730
47. C. Chatgilialoglu, D. Crich, M. Komatsu, and I. Ryu Chem. Rev. 99 1999 1991
48. Z. Shi, and F. Glorius Chem. Sci. 4 2013 829
49. Z. Liu, J. Zhang, S. Chen, E. Shi, Y. Xu, and X. Wan Angew. Chem., Int. Ed. 51 2012 3231
50. Copper(III) intermediates have been proposed for copper-catalyzed allylic oxidation of alkenes with peresters J. Eames, and M. Watkinson Angew. Chem., Int. Ed. 40 2001 3567
51. S.K. Rout, S. Guin, K.K. Ghara, A. Banerjee, and B.K. Patel Org. Lett. 14 2012 3982
52. W.-J. Yoo, and C.-J. Li J. Org. Chem. 71 2006 6266