Organocatalytic Nucleophilic Substitution Reaction of gem-Difluoroalkenes with Ketene Silyl Acetals

Azusa Kondoh, Kazumi Koda, Masahiro Terada*

*Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan, Email: mteradam.tohoku.ac.jp

A. Kondoh, K. Koda, M. Terada, Org. Lett., 2019, 21, 2277-2280.

DOI: 10.1021/acs.orglett.9b00566

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Abstract

Phosphazene P4-tBu effectively catalyzes a nucleophilic substitution reaction of gem-difluoroalkenes with ketene silyl acetals under mild conditions to provide monofluoroalkenes possessing an alkoxycarbonylmethyl group in high yields with high Z selectivities.

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proposed mechanism

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Key Words

vinyl fluorides, alkenylations, organocatalysis

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ID: J54-Y2019