Palladium-catalyzed aerobic acetoxylation of benzene using NOx-based redox mediators

Journal of Organometallic Chemistry

Volumn 793, Issue , 2015, Pages 263-268

  Zultanski, Susan L ^a   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Aerobic oxidation; Benzene; C H activation; Nitric acid; Palladium; Phenyl acetate

Indexed keywords

ACTIVATION ANALYSIS; BENZENE; CATALYSIS; NITRIC ACID; NITROGEN OXIDES; ORGANOMETALLICS; PALLADIUM;

AEROBIC OXIDATIONS; C-H ACTIVATION; NITRATE SOURCES; OPTIMIZED REACTION CONDITIONS; PALLADIUM-CATALYZED; PHENYL ACETATE; REDOX MEDIATORS; STOICHIOMETRIC OXIDANT;

PALLADIUM COMPOUNDS;

EID: 84939568439     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2015.03.003     Document Type: Article

References (51)

1. K. Weissermel, and H.-J. Arpe Industrial Organic Chemistry fourth ed. 2003 Wiley-VCH New York
2. M. Weber, M. Weber, and M. Kleine-Boymann Phenol Ullmann's Encycl. Ind. Chem. 26 2004 503 519
3. R.J. Schmidt App. Catal. A 280 2005 89 103
4. For a review on transition metal catalyzed synthesis of hydroxylated arenes, see: D.A. Alonso, C. Nájera, I.M. Pastor, and M. Yus Chem. Eur. J. 16 2010 5274 5284
5. K. Muñiz Angew. Chem. Int. Ed. 48 2009 9412 9423
6. T.W. Lyons, and M.S. Sanford Chem. Rev. 110 2010 1147 1169
7. K.M. Engle, T.-S. Mei, M. Wasa, and J.-Q. Yu Acc. Chem. Res. 45 2012 788 802
8. D.C. Powers, and T. Ritter Acc. Chem. Res. 45 2012 840 850
9. For a general review on C-H activation of simple arenes, including Pd-catalyzed processes, see: N. Kuhl, M.H. Hopkinson, J. Wencel-Delord, and F. Glorius Angew. Chem. Int. Ed. 51 2012 10236 10254
10. T. Yoneyama, and R.H. Crabtree J. Mol. Catal. A 108 1996 35 40
11. F. Shibahara, S. Kinoshita, and K. Nozaki Org. Lett. 6 2004 2437 2439
12. M.H. Emmert, A.K. Cook, Y.J. Xie, and M.S. Sanford Angew. Chem. Int. Ed. 50 2011 9409 9412
13. F. Tato, A. García-Domínguez, and D.J. Cárdenas Organometallics 32 2013 7487 7494
14. A.K. Cook, M.H. Emmert, and M.S. Sanford Org. Lett. 15 2013 5428 5431
15. J.B. Gary, A.K. Cook, and M.S. Sanford ACS Catal. 3 2013 700 703
16. B. Cornils, and W.A. Herrmann J. Catal. 216 2003 23 31
17. B. Lücke, K.V. Narayana, A. Martin, and K. Jähnisch Adv. Synth. Catal. 346 2004 1407 1484
18. L.N. Pachkovskaya, K.I. Matveev, G.N. Il'inich, and N.K. Eremenko Kinet. Catal. 18 1977 1040 1043
19. P. Liang, H. Xiong, H. Guo, and G. Yin Catal. Commun. 11 2010 560 562
20. T. Jintoku, H. Taniguchi, and Y. Fujiwara Chem. Lett. 1987 1865 1868
21. T. Jintoku, K. Takaki, Y. Fujiwara, Y. Fuchita, and K. Hiraki Bull. Chem. Soc. Jpn. 63 1990 438 441
22. H. Guo, Z. Chen, F. Mei, D. Zhu, H. Xiong, and G. Yin Chem. Asian J. 8 2013 888 891
23. L.C. Passoni, A.T. Cruz, R. Buffon, U. Schuchardt, and J. Mol Catal. A 120 1997 117 123
24. H.A. Burton, and I.V. Kozhevnikov J. Mol. Catal. A 185 2002 285 290
25. Ashland Oil, Inc., Ashland, KY. Manufacture of Aryl Esters. US Patent 4,465,633, August 14, 1984.
26. S. Mukhopadhyay, G. Rothenberg, G. Lando, K. Agbaria, M. Kazanci, and Y. Sasson Adv. Synth. Catal. 343 2001 455 459
27. T. Yokota, S. Sakaguchi, and Y. Ishii Adv. Synth. Catal. 344 2002 849 854
28. Y. Izawa, and S.S. Stahl Adv. Synth. Catal. 352 2010 3223 3229
29. L. Boisvert, M.C. Denney, S.K. Hanson, and K.I. Goldberg J. Am. Chem. Soc. 131 2009 15802 15814
30. J.R. Khusnutdinova, N.P. Rath, and L.M. Mirica J. Am. Chem. Soc. 134 2012 2414 2422
31. J.R. Khusnutdinova, F. Qu, Y. Zhang, N.P. Rath, and L.M. Mirica Organometallics 31 2012 4627 4630
32. F. Tang, Y. Zhang, N.P. Rath, and L.M. Mirica Organometallics 31 2012 6690 6696
33. 2, see: F. Qu, J.R. Khusnutdinova, N.P. Rath, and L.M. Mirica Chem. Commun. 50 2014 3036 3039
34. J. Zhang, E. Khaskin, N.P. Anderson, P.Y. Zavalij, and A.N. Vedernikov Chem. Commun. 2008 3625 3627
35. Y.-H. Zhang, and Y.-Q. Yu J. Am. Chem. Soc. 131 2009 14654 14655
36. D. Wang, P.Y. Zavalij, and A.N. Vedernikov Organometallics 32 2013 4882 4891
37. D.S. Bohle R.G. Hicks, The Nitrogen Oxides: Persistant Radicals and van der Waals Complex Dimers. In Stable Radicals: Fundamental and Applied Aspects of Odd-Electron Compounds 2010 John Wiley & Sons, Ltd. UK 147 171
38. Z. An, X. Pan, X. Liu, X. Han, and X. Bao J. Am. Chem. Soc. 128 2006 16028 16029
39. K.J. Stowers, A. Kubota, and M.S. Sanford Chem. Sci. 3 2012 3192 3195
40. T. Tisue, and W.J. Downs Chem. Commun. 1969 410
41. Asahi Kasei Co, Osaka, Japan. Process for Preparing Phenyl Esters of Aliphatic Carboxylic Acids. US Patent 3,772,383, November 13, 1973.
42. (PhOAc TON = 9 or less) Asahi Kasei Co., Tokyo, Japan. Process for Preparing Phenyl Acetate and Related Products. US Patent 3,887,608, June 3, 1975.
43. W. Zhang, S. Lou, Y. Liu, and Z. Xu J. Org. Chem. 78 2013 5932 5948
44. W. Zhang, D. Wu, J. Zhang, and Y. Liu Eur. J. Org. Chem. 2014 5827 5835
45. B. Majhi, D. Kundu, S. Ahammed, and B.C. Ranu Chem. Eur. J. 20 2014 9862 9866
46. T. Diao, and S.S. Stahl Polyhedron 84 2014 96 102
47. D. Wang, Y. Izawa, and S.S. Stahl J. Am. Chem. Soc. 136 2014 9914 9917
48. S.-i. Uchiumi, K. Ataka, and T. Matsuzaki J. Organomet. Chem. 576 1999 279 289
49. M. Theimann, E. Scheibler, and K.W. Weigland Nitric Acid, Nitrous Acid, and Nitrogen Oxides 2005 Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH Weinheim
50. W. Laue, M. Theimann, E. Schiebler, and K.W. Wiegland Nitrates and Nitrites 2005 Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH Weinheim
51. J. Campora, P. Palma, D. del Rio, E. Carmona, C. Graiff, and A. Tiripicchio Organometallics 22 2003 3345 3347