Abstract
An undecorated Co(OAc)2-catalyzed aerobic oxidation system has been reported that enables direct transformation of 4-benzylphenols into the corresponding 4-hydroxybenzophenones. The procedure is especially suitable for electron-withdrawing group-containing substrates, which are commonly inefficient to conduct this category of oxidation. Based on well-defined p-benzoquinone methides and the confirmed ethereal intermediate, a plausible mechanism was depicted.
Similar content being viewed by others
References
W.B. Huang, C.Y. Du, J.A. Jiang, Y.F. Ji, Res. Chem. Intermed. 39, 2849 (2013)
D.K. Palit, Res. Chem. Intermed. 31, 205 (2005)
P. Xiao, M.Z. Dai, J. Nie, J. Appl. Polym. Sci. 108, 665 (2008)
V.D. Chaube, P. Moreau, A. Finiels, A.V. Ramaswamy, A.P. Singh, Catal. Lett. 79, 89 (2002)
T. Suzuki, S. Kitamura, R. Khota, K. Sugihara, N. Fujimoto, S. Ohta, Toxicol. Appl. Pharmacol. 203, 9 (2005)
P. Xiao, S.Q. San, J. Nie, Polym. Adv. Technol. 19, 1305 (2008)
J.L. Yang, S.Q. Shi, F. Xu, J. Nie, Photochem. Photobiol. Sci. 12, 323 (2013)
M. Sodervall, M. Eloranta, A. Kalapudas, US 7812198B2 (2010)
P.L. Coe, C.E. Scriven, J. Chem. Soc. Perkin Trans. I, 475 (1986)
A. Heidekum, M.A. Harmer, W.F. Hoelderich, J. Catal. 176, 260 (1998)
V.D. Chaube, P. Moreau, A. Finiels, A.V. Ramaswamy, A.P. Singh, J. Mol. Catal. A Chem. 174, 255 (2001)
A.K. Tripathi, J.K. Sama, S.C. Taneja, Indian J. Chem. B 49, 379 (2010)
X. Sun, Z.M.A. Judeh, B.F. Ali, S.F. Alshahateet, Catal. Today 131, 423 (2008)
J. Hu, Y. Hu, J. Mao, J. Yao, Z. Chen, H. Li, Green Chem. 14, 2894 (2012)
J.A. Jiang, C. Chen, J.G. Huang, H.W. Liu, S. Cao, Y.F. Ji, Green Chem. 16, 1248 (2014)
J.A. Jiang, J.L. Du, D.H. Liao, Z.G. Wang, Y.F. Ji, Tetrahedron Lett. 55, 1406 (2014)
J.A. Ashenhurst, Chem. Soc. Rev. 39, 540 (2010)
S.E. Allen, R.R. Walvoord, R. Padilla-Salinas, M.C. Kozlowski, Chem. Rev. 113, 6234 (2013)
B. Barton, C.G. Logie, B.M. Schoonees, B. Zeelie, Org. Process Res. Dev. 9, 62 (2005)
J.A. Jiang, C. Chen, Y. Guo, D.H. Liao, X.D. Pan, Y.F. Ji, Green Chem. 16, 2807 (2014)
W. Baik, H.J. Lee, J.M. Jang, S. Koo, B.H. Kim, J. Org. Chem. 65, 108 (2000)
T. Iwahama, Y. Yoshino, T. Keitoku, S. Sakaguchi, Y. Ishii, J. Org. Chem. 65, 6502 (2000)
X. Baucherel, L. Gonsalvi, I.W.C.E. Arends, S. Ellwood, R.A. Sheldon, Adv. Synth. Catal. 346, 286 (2004)
A.J. Kresge, H.J. Chen, J. Am. Chem. Soc. 94, 2818 (1972)
A.J. Kresge, D.S. Sagatys, H.J. Chen, J. Am. Chem. Soc. 99, 7228 (1977)
Acknowledgments
We gratefully thank the National Natural Science Foundation of China (Project Nos. 21176074 and 21476074) and Research Fund for the Doctoral Program of Higher Education of China (Project No. 20130074110009) for financial support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Huang, JG., Guo, Y., Jiang, JA. et al. An eco-friendly Co(OAc)2-catalyzed aerobic oxidation of 4-benzylphenols into 4-hydroxybenzophenones. Res Chem Intermed 41, 7115–7124 (2015). https://doi.org/10.1007/s11164-014-1801-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-014-1801-8