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The solvent-controlled chemoselective construction of C–S/S–S bonds via the Michael reaction/thiol coupling of quinoline-2-thiones

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Abstract

K2CO3-catalyzed thio-Michael addition using quinoline-2-thiones and α,β-unsaturated carbonyl compounds was used to assess the chemoselective construction of C–S and S–S bonds under mild reaction conditions in different solvents. The C–S bond showed a better chemoselective construction in EtOH whereas the S–S bond showed a better chemoselective construction in 1,4-dioxane. The corresponding products, generated from the reaction, presented a significant solvent-controlling effect.

Graphical abstract: The solvent-controlled chemoselective construction of C–S/S–S bonds via the Michael reaction/thiol coupling of quinoline-2-thiones

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Publication details

The article was received on 28 Nov 2018, accepted on 31 Jan 2019 and first published on 31 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB02971G
Citation: Org. Biomol. Chem., 2019, Advance Article

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    The solvent-controlled chemoselective construction of C–S/S–S bonds via the Michael reaction/thiol coupling of quinoline-2-thiones

    X. Zhang, T. Wang, X. Liu, X. Wang and Z. Quan, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB02971G

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