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Issue 7, 2010
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Rhodium-catalyzed [2+2+2] cycloaddition of various fluorine-containing alkynes—novel synthesis of multi-substituted fluoroalkylated aromatic compounds

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Abstract

Treatment of various fluorinated internal alkynes with 10 mol% of RhCl3·H2O and 30 mol% of i-Pr2NEt in toluene at the reflux temperature for 18 h gave the corresponding trimerization products as an isomeric mixture in high yields. Cycloaddition using 1.0 equiv. of fluorinated alkynes and 2.0 equiv. of non-fluorinated alkynes under the same reaction conditions as in the trimerization led to mono- and bis-fluoroalkylated benzene derivatives in high yields, together with small amounts of trimerization products. The reaction of fluorine-containing bispropargyl ether with non-fluorinated alkynes took place smoothly to afford the corresponding bicyclic molecules in good to high yields.

Graphical abstract: Rhodium-catalyzed [2+2+2] cycloaddition of various fluorine-containing alkynes—novel synthesis of multi-substituted fluoroalkylated aromatic compounds

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Publication details

The article was received on 11 Dec 2009, accepted on 02 Feb 2010 and first published on 22 Feb 2010


Article type: Paper
DOI: 10.1039/B926192C
Citation: Org. Biomol. Chem., 2010,8, 1718-1724

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    Rhodium-catalyzed [2+2+2] cycloaddition of various fluorine-containing alkynes—novel synthesis of multi-substituted fluoroalkylated aromatic compounds

    T. Konno, K. Moriyasu, R. Kinugawa and T. Ishihara, Org. Biomol. Chem., 2010, 8, 1718
    DOI: 10.1039/B926192C

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