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α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals

Xu Wang, Zijun Wu and Jian Wang*

*Department of Pharmacology and Pharmaceutical Science, School of Medicine, Tsinghua University, Beijing 117543, China, Email: wangjian2012tsinghua.edu.cn

X. Wang, Z. Wu, J. Wang, Org. Lett., 2016, 18, 576-579.

DOI: 10.1021/acs.orglett.5b03615 (free Supporting Information)


Abstract

With a suitable combination of N-heterocyclic carbene precatalyst, base, and fluorine reagent, a fluorination of alkynals proceeded smoothly to yield a wide range of α-fluoroallenoates with excellent chemoselectivity. α-Fluorinated allenoates are versatile synthetic intermediates toward other useful fluorine-containing building blocks.

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Key Words

allenes, fluorination, NFSI, organocatalysis


ID: J54-Y2016