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Issue 11, 2018
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Reductive ortho C–H cyanoalkylation of aryl(heteroaryl) sulfoxides: a general approach to α-aryl(heteroaryl) nitriles

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Abstract

A general protocol for the synthesis of α-aryl- and heteroaryl nitriles has been developed. Specifically, the simple treatment of a mixture of aryl(heteroaryl) sulfoxides and α-stannyl nitriles with an anhydride produces a diverse array of α-aryl(heteroaryl) nitriles. Notable features of this reaction include its remarkably low reaction temperature (−78 °C), superior functional group compatibility, and highly transformable products. A DFT mechanistic study indicates that a counter anion (OCOCF3) extracting the SnBu3 group from a nitrilium–sulfurane adduct promotes the rapid formation of a ketenimine-sulfonium salt, which undergoes a facile dearomative Claisen-type rearrangement to form the product.

Graphical abstract: Reductive ortho C–H cyanoalkylation of aryl(heteroaryl) sulfoxides: a general approach to α-aryl(heteroaryl) nitriles

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Publication details

The article was received on 12 Mar 2018, accepted on 12 Apr 2018 and first published on 24 Apr 2018


Article type: Research Article
DOI: 10.1039/C8QO00268A
Citation: Org. Chem. Front., 2018,5, 1756-1762
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    Reductive ortho C–H cyanoalkylation of aryl(heteroaryl) sulfoxides: a general approach to α-aryl(heteroaryl) nitriles

    F. Luo, Y. Lu, M. Hu, J. Tian, L. Zhang, W. Bao, C. Yan, X. Huang, Z. Wang and B. Peng, Org. Chem. Front., 2018, 5, 1756
    DOI: 10.1039/C8QO00268A

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