Issue 9, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
26 Ker. 2018
Accepted
07 Cʼhwe. 2019
First published
07 Cʼhwe. 2019

Org. Biomol. Chem., 2019,17, 2542-2547

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, 17, 2542 DOI: 10.1039/C8OB03201G

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