Synthesis of a Novel Zirconium Oligostyrenylphosphonate-Phosphate and its Application in Asymmetric Epoxidation

Springer Science and Business Media LLC - Tập 21 - Trang 276-282 - 2011
Yunfei Luo1, Xiangkai Fu1, Xiaochuan Zou1,2, Changwei Wang1, Xiaoyan Hu1, Ziyong Jia1, Huaizhi Zhang1
1College of Chemistry and Chemical Engineering, Research Institute of Applied Chemistry Southwest University, The Key Laboratory of Applied Chemistry of Chongqing Municipality, The Key Laboratory of Eco-environments in Three Gorges Reservoir Region (Ministry of Education), Chongqing, People’s Republic of China
2Department of Biological & Chemical Engineering, Chongqing Education College, Chongqing, People’s Republic of China

Tóm tắt

The layered crystalline zirconium oligostyrenylphosphonate-phosphate (LCZSPP) was synthesized in the presence of HF for the first time, and this compound was well characterized by FT-IR, TG, SEM, TEM, XPS and XRD. The LCZSPP possessed high thermal stability by TG. SEM and TEM demonstrated that this compound is a typically layered crystalline compound with basically regular shape. XRD data also showed that the interlayer spacing (10.65 Å) of the sample was 3.01 Å more than the α-ZrP (7.64 Å). Moreover, chiral Jacobsen’s catalyst was axially immobilized onto LCZSPP by a diamine linker group. All the synthesized heterogeneous catalysts exhibited excellent reactivity and enantioselectivity in the asymmetric epoxidation of simple olefins.

Tài liệu tham khảo

W. Zhang, J.L. Loebach, S.R. Wilson, E.N. Jacobsen, J. Am. Chem. Soc. 112, 2801 (1990)

R. Irie, K. Noda, Y. Ito, N. Matsumoto, T. Katsuki, Tetrahedron Lett. 31, 7345 (1990)

H. Zhang, C. Li, Tetrahedron 62, 6640 (2006)

L. Canali, D.C. Sherrington, Chem. Soc. Rev. 28, 85 (1999)

M. Heitbaum, F. Glorius, I. Escher, Angew. Chem. Int. Ed. 45, 4732 (2006)

C. Baleizo, H. Garcia, Chem. Rev. 106, 3987 (2006)

E.M. Mcgarrigle, D.G. Gilheany, Chem. Rev. 105, 1563 (2005)

J.M. Fraile, J.I. Garci, J.A. Mayoral, Chem. Rev. 109, 360 (2009)

A. Clearfield, D.S. Thakur, Appl. Catal. A 26, 1 (1986)

S. Nakayama, K.J. Itoh, J. Eur. Ceram. Soc. 23, 1047 (2003)

R.Q. Zeng, X.K. Fu, Y. Sui, X.B. Yang, M.D. Sun, J.R. Chen, J. Organomet. Chem. 693, 2666 (2008)

U. Costantino, M. Nocchetti, R. Vivani, J. Am. Chem. Soc. 124, 8428 (2002)

T.M. Suzuki, S. Kobayashi, D.A. Pacheco Tanaka, M.A. Llosa Tanco, T. Nagase, Y. Onodera, React. Funct. Polym. 58, 131 (2004)

A.A. Marti, J.L. Colon, Inorg. Chem. 42, 2830 (2003)

I.O. Benftez, B. Bujoli, L.J. Camus, C.M. Lee, F. Odobel, D.R. Talham, J. Am. Chem. Soc. 124, 4363 (2002)

I.C. Marcu, I. Sandulescu, J.M.M. Millet, Appl. Catal. A 227, 309 (2002)

M. Curini, F. Montanari, O. Rosati, E. Lioy, R. Margarita, Tetrahedron Lett. 44, 3923 (2003)

Z.K. Wang, J.M. Hissing, A. Clearfield, J. Am. Chem. Soc. 125, 10375 (2003)

X.J. Wu, X.B. Ma, Y.L. Ji, Q. Wang, X. Jia, X.K. Fu, J. Mol. Catal. A Chem. 265, 316 (2007)

M. Niehues, G. Kehr, G. Erker, B. Wibbeling, R. Frohlich, O. Blacque, H. Berke, J. Organomet. Chem. 663, 192 (2002)

W.S. Ren, X.K. Fu, H.B. Bao, R.F. Bai, P.P. Ding, B.L. Sui, Catal. Commun. 10, 788 (2009)

X.B. Tu, X.K. Fu, X.Y. Hu, Y.D. Li, Inorg. Chem. Commun. 13, 404 (2010)

B.W. Gong, X.K. Fu, J.X. Chen, Y.D. Li, X.C. Zou, X.B. Tu, J. Catal. 262, 9 (2009)

X.B. Ma, J. Liu, L.S. Xiao, R. Cheng, J.Q. Zhou, X.K. Fu, J. Mater. Chem. 19, 1098 (2009)

X.C. Zou, X.K. Fu, Y.D. Li, X.B. Tu, S.D. Fu, Y.F. Luo, X.J. Wu, Adv. Synth. Catal. 352, 163 (2010)

G.J. Kim, J.H. Shina, Tetrahedron Lett. 40, 6827 (1999)

M. Palncki, P.J. Pospisil, W. Zhang, E.N. Jacobsen, J. Am. Chem. Soc. 116, 9333 (1994)

Y. Sui, X.N. Fang, R.H. Hu, Y.P. Xu, X.C. Zhou, X.K. Fu, Mater. Lett. 61, 1354 (2007)

A.R. Silva, J.L. Figueiredo, C. Freire, B.D. Castro, Micropor. Mesopor. Mater. 68, 83 (2004)

W. Zhang, N.H. Lee, E.N. Jacobsen, J. Am. Chem. Soc. 116, 425 (1994)

H.D. Zhang, S. Xiang, J.L. Xiao, C. Li, J. Mol. Catal. A Chem. 238, 175 (2005)

R.I. Kureshy, I. Ahamd, N.H. Khan, S.H.R. Abdi, S. Singh, P.H. Pandia, J. Catal. 235, 28 (2005)