Synthesis of Organofluoro Compounds Using Methyl Perfluoroalk-2-ynoates as Building Blocks

Xuechun Sun; Jing Han; Jie Chen; Hui Zhang; Weiguo Cao

doi:10.1002/tcr.201500258

Synthesis of Organofluoro Compounds Using Methyl Perfluoroalk-2-ynoates as Building Blocks

Chem Rec. 2016 Apr;16(2):907-23. doi: 10.1002/tcr.201500258. Epub 2016 Mar 10.

Authors

Xuechun Sun¹, Jing Han¹, Jie Chen¹, Hui Zhang^{1

2}, Weiguo Cao^{1

3

4

5}

Affiliations

¹ Department of Chemistry, Innovative Drug Research Center Shanghai University, Shanghai, 200444, P. R. China.
² Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai, 200444, P. R. China.
³ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, Shanghai, 200032, P. R. China.
⁴ Key Laboratory of Synthetic Organic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, Shanghai, 200032, P. R. China.
⁵ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, Shanghai, 200032, P. R. China.

PMID: 26969042
DOI: 10.1002/tcr.201500258

Abstract

This review provides an overview of several synthetic applications of methyl perfluoroalk-2-ynoates, leading to convenient preparation of many perfluoroalkylated compounds. The use of these important substrates in the synthesis of various five-, six-, and seven-membered heterocycles, cyclopentadienes, and biphenyls is described, alongside a discussion of the mechanistic aspects of these reactions.

Keywords: Michael addition; drug design; fluorine; perfluoroalkyl groups; synthetic methods.

Publication types

Research Support, Non-U.S. Gov't