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Synfacts 2008(7): 0770-0770  
DOI: 10.1055/s-2008-1078434
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Polymer-Supported Gadolinium Triflate as a Lewis Acid Catalyst

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Hidetoshi Ohta
H.-J. Yoon, S.-M. Lee, J.-H. Kim, H.-J. Cho, J.-W. Choi, S.-H. Lee, Y.-S. Lee*
Seoul National University and Catholic University of Daegu, Gyeongsan, Korea
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Publication History

Publication Date:
20 June 2008 (online)

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Significance

Polymer-supported gadolinium triflate (CMPS-IM-Gd) was prepared and found to be an efficient Lewis acid catalyst for the acetylation of various alcohols and phenols with acetic anhydride. Thus, the reaction of Merrifield resin (chloromethyl polystyrene, CMPS) with 1-methyl­imidazole (1.5 equiv) gave CMPS-IM. After the reaction of CMPS-IM with KOt-Bu, the resulting resin was treated with Gd(OTf)3 to afford the CMPS-IM-Gd catalyst. The acetylation of alcohols and phenols with acetic anhydride was carried out in the presence of the CMPS-IM-Gd catalyst (0.5 mol % Gd) to give the corresponding acetylated products in 14 to >99% yield (31 examples).