Gengxiu Zheng et al.
FULL PAPERS
Typically, 2 mL (16 mmol) ethylbenzene, 10 mL acetonitrile,
the desired amount of DMG and NHPI were added into the
autoclave. The reactor was flushed three times with O2 and
pressurized to 0.3 MPa, and then heated to the desired tem-
perature with stirring. During the reaction the O2 pressure
was kept constant by supplying dioxygen.
Rev. 2007, 107, 2546–2562; d) A. A. Fokin, P. R.
Schreiner, Adv. Synth. Catal. 2003, 345, 1035–1052;
e) J. M. Thomas, R. Raja, Chem. Commun. 2001, 8,
675–687.
[3] a) F. Recupero, C. Punta, Chem. Rev. 2007, 107, 3800–
3842; b) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth.
Catal. 2001, 343, 393–427; c) R. A. Sheldon, I. W. C. E.
Arends, Adv. Synth. Catal. 2004, 346, 1051–1071; d) C.
Galli, P. Gentili, O. Lanzalunga, Angew. Chem. 2008,
120, 4868–4874; Angew. Chem. Int. Ed. 2008, 47, 4790–
4796; e) Y. Aoki, S. Sakaguchi, Y. Ishii, Tetrahedron
2006, 62, 2497–2500; f) G. Y. Yang, L. W. Zheng, G. H.
Wu, X. S. Lin, M. P Song, Adv. Synth. Catal. 2007, 349,
2445–2448; g) R. A. Sheldon, I. W. C. E. Arends, J.
Mol. Catal. A: Chem. 2006, 251, 200–214.
The oxidation products were identified by GC-MS and
quantified by GC. The conversion of ethylbenzene, and the
selectivities of acetophenone (AcPO) and 1-phenylethanol
(PEA) were determined by calibration curves. The yield of
1-phenylethyl hydroperoxide (PEHP) could not be directly
measured by GC due to its decomposition to AcPO in GC
analysis.[10] In addition, PEHP can be converted quantita-
tively to PEA by excess Ph3P at room temperature.[6,10] Thus
the amount of PEHP can be accurately quantified by treat-
ment of the mixture with excess Ph3P for 1 h and a second
GC measurement. For all the other substrates, the conver-
sions and selectivities were calculated by GC calibration
curves.
[4] Y. Aoki, S. Sakaguchi, Y. Ishii, Adv. Synth. Catal. 2004,
346, 199–202.
[5] S. Tsujimoto, S. Sakaguchi, Y. Ishii, Tetrahedron Lett.
2003, 44, 5601.
[6] a) G. Y. Yang, Y. F. Ma, J. Xu, J. Am. Chem. Soc. 2004,
126,10542; b) G. Y. Yang, Q. H. Zhang, H. Miao, X. L.
Tong, J. Xu, Org. Lett. 2005, 7, 263–266; c) Q. H.
Zhang, C. Chen, H. Ma, H. Miao, W. Zhang, Z. Q. Sun,
J. Xu, J. Chem. Technol. Biotechnol. 2008, 83, 1364–
1369.
Acknowledgements
We gratefully acknowledge the financial support from the De-
velopment Programs in Science and Technology of Shan
Dong (2008GG10002021).
[7] Z. T. Du, Z. Q. Sun, W. Zhang, H. Miao, H. Ma, J. Xu,
Tetrahedron Lett. 2009, 50, 1677–1680.
[8] X. L. Tong, J. Xu, H. Miao, J. Gao, Tetrahedron Lett.
2006, 47, 1763–1766.
[9] K. Matsunaka, T. Iwahama, S. Sakaguchi, Y. Ishii, Tet-
rahedron Lett. 1999, 40, 2165–2168.
References
[10] S. Evans, J. R. L. Smith, J. Chem. Soc. Perkin Trans. 2
[1] a) P. R. Schreiner, A. A. Fokin, Chem. Rec. 2004, 3,
247–257; b) E. N. Jacobson, Adv. Synth. Catal. 2004,
346, 109; c) M. Beller, Adv. Synth. Catal. 2004, 346,
107–108;.
2001, 174–180.
[11] H. Ma, J. Xu, Q. H. Zhang, H. Miao, W. H. Wu, Catal.
Commun. 2007, 8, 27–30.
[12] T. Iwahama, G. Hatta, S. Sakaguchi, Y. Ishii, Chem.
[2] a) T. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev.
2005, 105, 2329–2363; b) A. K. Suresh, M. M. Sharma,
T. Sridhar, Ind. Eng. Chem. Res. 2000, 39, 3958–3997;
c) C. I. Herrerias, X. Q. Yao, Z. P. Li, C. J. Li, Chem.
Commun. 2000, 163–164.
[13] 13] N. Koshino, Y. Cai, J. H. Espenson, J. Phys. Chem.
A: 2003, 107, 4262–4267.
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Adv. Synth. Catal. 2009, 351, 2638 – 2642