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Issue 23, 2016
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Silver-initiated radical ring expansion/fluorination of ethynyl cyclobutanols: efficient synthesis of monofluoroethenyl cyclopentanones

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Abstract

A stereoselective synthesis of β-halogenated 2-methylenecyclopentanones via silver-catalyzed formal ring expansion using water as the cosolvent is described. A variety of 2-methylenecyclopentanones with fluoro, chloro and bromo functionalities are efficiently prepared from 1-alkynyl cyclobutanols. This method offers facile access to halogenated complex molecules which are not only useful chemicals but also valuable building blocks for further derivatizations.

Graphical abstract: Silver-initiated radical ring expansion/fluorination of ethynyl cyclobutanols: efficient synthesis of monofluoroethenyl cyclopentanones

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Publication details

The article was received on 23 Sep 2016, accepted on 17 Oct 2016 and first published on 18 Oct 2016


Article type: Communication
DOI: 10.1039/C6GC02656G
Citation: Green Chem., 2016,18, 6236-6240
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    Silver-initiated radical ring expansion/fluorination of ethynyl cyclobutanols: efficient synthesis of monofluoroethenyl cyclopentanones

    Q. Tian, B. Chen and G. Zhang, Green Chem., 2016, 18, 6236
    DOI: 10.1039/C6GC02656G

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