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(E)-Selective Friedel–Crafts acylation of alkynes to β-chlorovinyl ketones: defying isomerizations in batch reactions by flow chemistry approaches

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Abstract

The Friedel–Crafts acylation of alkynes stereoselectively provides (Z)-β-chlorovinyl ketones, whereas the AlCl3-promoted reaction yields a mixture of stereoisomeric β-chlorovinyl ketones. To develop the (E)-selective synthesis of β-chlorovinyl ketones, a flow chemistry approach was devised for the Friedel–Crafts acylation of alkynes that defies the facile (E) → (Z) isomerization under the AlCl3-promoted reaction conditions. Compared to batch reactions, the flow chemistry approach provides a fast, clean, high yielding, and stereoselective synthetic route to (E)-β-chlorovinyl ketones.

Graphical abstract: (E)-Selective Friedel–Crafts acylation of alkynes to β-chlorovinyl ketones: defying isomerizations in batch reactions by flow chemistry approaches

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Publication details

The article was received on 07 Feb 2019, accepted on 04 Apr 2019 and first published on 11 Apr 2019


Article type: Research Article
DOI: 10.1039/C9QO00217K
Citation: Org. Chem. Front., 2019, Advance Article

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    (E)-Selective Friedel–Crafts acylation of alkynes to β-chlorovinyl ketones: defying isomerizations in batch reactions by flow chemistry approaches

    H. Koo, H. Y. Kim and K. Oh, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00217K

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