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Ru(II)-Catalysed synthesis of (1H)-isothiochromenes by oxidative coupling of benzylthioethers with internal alkynes

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Abstract

The synthesis of 1H-isothiochromenes by oxidative coupling of benzyl(tert-butyl)thioethers with internal alkynes, catalysed by Ru(II), has been achieved. The reaction occurs by S-directed C–H activation at the ortho position of the aryl ring, promoted by ruthenium, migratory insertion of the alkyne, 1,2-thio-Wittig rearrangement of the tert-butyl group and reductive elimination by C–S coupling between the resulting anionic sulfide and the vinylic carbon.

Graphical abstract: Ru(ii)-Catalysed synthesis of (1H)-isothiochromenes by oxidative coupling of benzylthioethers with internal alkynes

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Publication details

The article was received on 26 Dec 2018, accepted on 07 Feb 2019 and first published on 07 Feb 2019


Article type: Paper
DOI: 10.1039/C8OB03201G
Citation: Org. Biomol. Chem., 2019, Advance Article

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    Ru(II)-Catalysed synthesis of (1H)-isothiochromenes by oxidative coupling of benzylthioethers with internal alkynes

    E. P. Urriolabeitia and S. Ruiz, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB03201G

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