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Pd-Catalyzed intramolecular C–H addition to the cyano-group: construction of functionalized 2,3-fused thiophene scaffolds

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Abstract

An efficient synthesis of 2,3-fused thiophenes was demonstrated through a Pd-catalyzed intramolecular C–H addition of thiophenes bearing cyanohydrin components at the C(3) positions to nitriles. A diversity of functionalized fused thiophenes with saturated six-, seven- or eight-membered rings can be prepared in good to excellent yields. This method can also be applied to prepare fused pyrrole and furan analogues through the use of different heteroarene scaffolds. Further demonstration of the synthetic utility of this Pd-catalyzed cyclization was explored.

Graphical abstract: Pd-Catalyzed intramolecular C–H addition to the cyano-group: construction of functionalized 2,3-fused thiophene scaffolds

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Publication details

The article was received on 06 Nov 2017, accepted on 24 Nov 2017 and first published on 27 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QO01000A
Citation: Org. Chem. Front., 2018, Advance Article
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    Pd-Catalyzed intramolecular C–H addition to the cyano-group: construction of functionalized 2,3-fused thiophene scaffolds

    L. Zhao and W. Liao, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO01000A

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