Ru(ii)-Catalysed synthesis of (1H)-isothiochromenes by oxidative coupling of benzylthioethers with internal alkynes
Esteban P Urriolabeitia1, Sara Ruiz
1Instituto de Síntesis Química y Catálisis Homogénea, ISQCH, CSIC-Universidad de Zaragoza, Pedro Cerbuna 12, 50009 Zaragoza, Spain. esteban@unizar.es.
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.
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