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Microwave-assisted synthesis of hydroxyl-containing isoquinolines by metal-free radical cyclization of vinyl isocyanides with alcohols

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Abstract

A convenient microwave-assisted protocol for the synthesis of hydroxyl-containing isoquinolines from a metal-free radical cyclization reaction of vinyl isonitriles with alcohols was developed with moderate-to-excellent yields. Vinyl isonitriles are coupled with alkyl radicals through direct catalytic functionalization of the α sp3 C–H bond of alcohols. The methodology demonstrates a broad substrate scope, shows excellent functional group tolerance, is highly atom-economical and highly efficient, thus enabling the preparation of diverse potentially valuable hydroxyl-containing isoquinolines.

Graphical abstract: Microwave-assisted synthesis of hydroxyl-containing isoquinolines by metal-free radical cyclization of vinyl isocyanides with alcohols

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Publication details

The article was received on 04 Sep 2017, accepted on 02 Nov 2017 and first published on 02 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB02221B
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Microwave-assisted synthesis of hydroxyl-containing isoquinolines by metal-free radical cyclization of vinyl isocyanides with alcohols

    D. Xue, H. Chen, Y. Xu, H. Yu, L. Yu, W. Li, Q. Xie and L. Shao, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02221B

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