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Issue 35, 2012
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Synthesis of (Z)-3-aryloxy-acrylonitriles, (E)-3-aryloxy-acrylonitriles and 3-cyanobenzofurans through the sequential reactions of phenols with propiolonitriles

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Abstract

A Na2CO3-promoted addition of phenols to propiolonitriles generated (Z)-3-aryloxy-acrylonitriles in nearly quantitative yields with exclusively Z-isomers, and a DABCO-promoted addition reaction of phenols with propiolonitriles afforded mainly (E)-3-aryloxy-acrylonitriles with high yields. The obtained (E)-3-aryloxy-acrylonitriles underwent intramolecular cyclization to give 3-cyanobenzofurans in good yields through palladium-catalyzed direct C–H bond functionalization.

Graphical abstract: Synthesis of (Z)-3-aryloxy-acrylonitriles, (E)-3-aryloxy-acrylonitriles and 3-cyanobenzofurans through the sequential reactions of phenols with propiolonitriles

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Publication details

The article was received on 19 May 2012, accepted on 03 Jul 2012 and first published on 05 Jul 2012


Article type: Paper
DOI: 10.1039/C2OB25969A
Citation: Org. Biomol. Chem., 2012,10, 7184-7196
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    Synthesis of (Z)-3-aryloxy-acrylonitriles, (E)-3-aryloxy-acrylonitriles and 3-cyanobenzofurans through the sequential reactions of phenols with propiolonitriles

    W. Zhou, Y. Zhang, P. Li and L. Wang, Org. Biomol. Chem., 2012, 10, 7184
    DOI: 10.1039/C2OB25969A

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