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Selective synthesis of aryl thioamides and aryl-α-ketoamides from α-oxocarboxylic acids and tetraalkylthiuram disulfides: an unexpected chemoselectivity from aryl sulfonyl chlorides

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Abstract

Aryl sulfonyl chloride-controlled generation of aryl thioamides and aromatic α-ketoamides through base-promoted decarboxylative functionalization of α-oxocarboxylic acids with tetraalkylthiuram disulfides has been established. The diverse formation of these two products could be controlled by the addition of tosyl chloride in different solvents. This protocol is compatible with a variety of electron-donating and electron-withdrawing functional groups and provides an attractive means to produce aryl thioamides and aromatic α-ketoamides with moderate to excellent yields.

Graphical abstract: Selective synthesis of aryl thioamides and aryl-α-ketoamides from α-oxocarboxylic acids and tetraalkylthiuram disulfides: an unexpected chemoselectivity from aryl sulfonyl chlorides

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Publication details

The article was received on 18 Oct 2018, accepted on 23 Dec 2018 and first published on 25 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QO01127C
Citation: Org. Chem. Front., 2019, Advance Article
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    Selective synthesis of aryl thioamides and aryl-α-ketoamides from α-oxocarboxylic acids and tetraalkylthiuram disulfides: an unexpected chemoselectivity from aryl sulfonyl chlorides

    M. Lai, Z. Wu, Y. Wang, Y. Zheng and M. Zhao, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01127C

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