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Synthesis of Functionalized Furans via Chemoselective Reduction/Wittig Reaction Using Catalytic Triethylamine and Phosphine

Chia-Jui Lee, Tzu-Hsiu Chang, Jhen-Kuei Yu, Ganapuram Madhusudhan Reddy, Ming-Yu Hsiao and Wenwei Lin*

*Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan ROC, Email: wenweilinntnu.edu.tw

C.-J. Lee, T.-H. Chang, J. K. Yu, G. M. Reddy, M.-Y. Hsiao, W. Lin, Org. Lett., 2016, 18, 3758-3761.

DOI: 10.1021/acs.orglett.6b01781 (free Supporting Information)


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Abstract

Catalytic amounts of phosphine and triethylamine enable an efficient protocol for the synthesis of highly functionalized furans via intramolecular Wittig reaction. Silyl chloride as the initial promoter activates the phosphine oxide for reduction, while decomposition of Et3N·HCl resulted in regeneration of base, which mediated formation of phosphorus ylide.


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proposed reaction mechanism



Key Words

furans, Wittig reaction, phenylsilane, organocatalysis


ID: J54-Y2016