Table 4 PE-2 as a recoverable and reusable catalyst for Wittig
reaction
W. J. Marshall, B. M. Fish, M. F. Schiffhauer and F. Davidson,
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3 For applications of Wittig-reaction in organic synthesis, see:
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Run
Yield (%)
E/Z
Run
Yield (%)
E/Z
1
2
3
99
99
94
499 : 1
499 : 1
499 : 1
4
5
96
98
499 : 1
499 : 1
4 B. M. Trost, Science, 1991, 254, 1471.
5 For catalytic arsenic ylide olefination, see: (a) P. Cao, C.-Y. Li,
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72, 6628; (b) L. Shi, W. Wang, Y. Wang and Y. Huang, J. Org.
Chem., 1989, 54, 2027.
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X.-Q. Wen, J. Chem. Soc., Perkin Trans. 1, 1989, 2397.
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8 For selected arsonium ylide olefination, see: (a) D. Habrant,
B. Stengel, S. Meunier and C. Mioskowski, Chem.–Eur. J., 2007,
13, 5433; (b) S. Zhu, Y. Liao and S. Zhu, Org. Lett., 2004, 6, 377;
(c) W.-M. Dai, A. Wu and H. Wu, Tetrahedron: Asymmetry, 2002,
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(e) A. Seyer, L. Alcaraz and C. Mioskowski, Tetrahedron Lett.,
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Y.-L. Wu, J. Chem. Soc., Perkin Trans. 1, 1996, 1057;
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Scheme 1 Synthesis of UV-light absorbing reagent 7.
realized for the first time. Even for diphenylketone and
hex-5-en-2-one, high yields were obtained. Both aromatic alde-
hydes and aliphatic aldehydes work well for such an olefination
with excellent yields and stereoselectivities. EDA, diazo aceto-
phenone, and ethyl 2-diazopropanoate are good reagents for the
olefination. Thus it provides an easy access to 1,2-disubstituted
alkenes, 1,1,2-trisubstituted alkenes, and 1,1,2,2-tetrasubstituted
alkenes with high stereoselectivity. The loading of PE-supported
catalyst could be reduced down to 0.05 mol% in the presence of the
cheap reducing agent PHMS and the PE-supported arsine was
recoverable and reusable, making the current reaction atom-
economic and potentially practically useful in organic synthesis.
We are grateful for the financial support from the National
Natural Science Foundation of China (No. 20821002 and
20932008), the Major State Basic Research Development
Program (Grant No. 2009CB825300), NSFC/RGC Joint
Research Scheme (Grant No. 21061160493 to YT and
N_CUHK470/10 to ZX) and Chinese Academy of Sciences.
P. Wang and C.-R. Liu have equal contribution to this paper.
9 Selected examples for polyethylene as
a catalyst carrier, see:
(a) D. E. Bergbreiter, Chem. Rev., 2002, 102, 3345; (b) X.-H. Yang,
C.-R. Liu, C. Wang, X.-L. Sun, Y.-H. Guo, X.-K. Wang, Z. Wang,
Z. Xie and Y. Tang, Angew. Chem., Int. Ed., 2009, 48, 8099;
(c) A. M. Kawaoka and T. J. Marks, J. Am. Chem. Soc., 2005,
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J. P. Tam and R. B. Merrifields, J. Am. Chem. Soc., 1989, 111, 8024;
(e) D. E. Bergbreiter and R. Chandran, J. Am. Chem. Soc., 1987,
109, 174.
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c
292 Chem. Commun., 2012, 48, 290–292
This journal is The Royal Society of Chemistry 2012