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Synfacts 2006(11): 1186-1186  
DOI: 10.1055/s-2006-949405
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

A Polymer-Supported Fe-Zr Catalyst for Dehydrative Esterfication

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada
Y. Nakamura, T. Maki, X. Wang, K. Ishihara*, H. Yamamoto*
Nagoya University, Japan, and The University of Chicago, USA
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Publication History

Publication Date:
24 October 2006 (online)

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Significance

A polystyrene-bound pyridinium triflylimide salt with iron and zirconium ions was developed as a recyclable catalyst for a dehydrative esterification reaction. Thus, the reaction of 4-phenylbutyric acid (5 mmol) and benzyl alcohol (5 mmol) with Zr(Oi-Pr)4 (0.05 mmol), Fe(Oi-Pr)3 (0.05 mmol) and 1 (3.5 mmol of pyridinium ion) in heptane was performed under refluxing conditions to give 4a in 91% yield. The polymer-supported Zr-Fe catalyst was reused nine times without loss of catalytic activity. No racemization occurred in the 4th consecutive reaction of (R)-2-phenylpropio­nic acid (98% ee) with benzyl alcohol to afford 4b in >99% yield with 98% ee.