Catalytic Domino Reaction of Ketones/Aldehydes with Me₃SiCF₂Br for the Synthesis of α-Fluoroenones/α-Fluoroenals

Xiaoning Song, Jian Chang, Dongsheng Zhu*, Jiaheng Li, Cong Xu, Qun Liu* and Mang Wang*

*Department of Chemistry, Northeast Normal University, Renmin Street 5268, Changchun 130024, P. R. China, Email: zhuds206nenu.edu.cn, liuqunnenu.edu.cn, wangm452nenu.edu.cn

X. Song, J. Chang, D. Zhu, J. Li, C. Xu, Q. Liu, M. Wang, Org. Lett., 2015, 17, 1712-1715.

DOI: 10.1021/acs.orglett.5b00488

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Abstract

A domino reaction of enolizable carbonyl compounds with Me₃SiCF₂Br provides α-fluoroenones and α-fluoroenals via formation of difluorocarbene and silyl enol ether, difluorocyclopropanation, desilylation, ring-opening, and defluorination. Me₃SiCF₂Br acts as not only the difluorocarbene source but also the TMS transfer agent as well as internal bromide and fluoride anion catalyst. Only a catalytic amount of n-Bu₄NBr as initiator is needed.

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Key Words

enones, vinyl fluorides

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ID: J54-Y2015