Efficient Synthesis of β-Chlorovinylketones from Acetylene in Chloroaluminate Ionic Liquids

Efficient Synthesis of β-Chlorovinylketones from Acetylene in Chloroaluminate Ionic Liquids

A method for the Friedel–Crafts-type insertion reaction of acetylene with acid chlorides in chloroaluminate ionic liquids is presented. The use of ionic liquids not only serves to avoid the use of carbon tetrachloride or 1,2-dichloroethane but also suppresses side reactions, notably the polymerizati...

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Veröffentlicht in:Organic letters 2011-08, Vol.13 (15), p.4048-4051
Hauptverfasser: Snelders, Dennis J. M, Dyson, Paul J
Format: Artikel
Sprache:eng
Schlagworte:
Acetylene - chemistry
Aluminum - chemistry
Chlorine - chemistry
Ionic Liquids - chemistry
Ketones - chemical synthesis
Molecular Structure
Vinyl Compounds - chemical synthesis
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Zusammenfassung:A method for the Friedel–Crafts-type insertion reaction of acetylene with acid chlorides in chloroaluminate ionic liquids is presented. The use of ionic liquids not only serves to avoid the use of carbon tetrachloride or 1,2-dichloroethane but also suppresses side reactions, notably the polymerization of acetylene, which occurs in these chlorinated solvents. Consequently, the products can be isolated using a simpler purification procedure, giving a range of aromatic and aliphatic β-chlorovinyl ketones in high yield and purity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201182t