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Eosin Y catalyzed difunctionalization of styrenes using O2 and CS2: a direct access to 1,3-oxathiolane-2-thiones

spectroscopy, SYNTHESIS

May 212016

Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC00924G, Paper

Arvind K. Yadav, Lal Dhar S. Yadav
An efficient, one-pot, highly regioselective synthesis of 1,3-oxathiolane-2-thiones from styrenes, CS₂, atmospheric O₂ and visible light is reported.

Eosin Y catalyzed difunctionalization of styrenes using O2 and CS2: a direct access to 1,3-oxathiolane-2-thiones

http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C6GC00924G?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Paper

Eosin Y catalyzed difunctionalization of styrenes using O₂ and CS₂: a direct access to 1,3-oxathiolane-2-thiones

Arvind K. Yadav^a and Lal Dhar S. Yadav*^a

*Corresponding authors

^aGreen Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad-211002, India
E-mail: ldsyadav@hotmail.com
Fax: +91 5322460533
Tel: +91 5322500652

Green Chem., 2016, Advance Article

DOI: 10.1039/C6GC00924G

Visible light promoted straightforward highly regioselective synthesis of 1,3-oxathiolane-2-thiones (cyclic dithiocarbonates) starting directly from styrenes, CS₂ and air (O₂) is reported. The protocol utilizes eosin Y as an organophotoredox catalyst and clean resources like visible light and air (O₂) as sustainable reagents at room temperature in a one-pot procedure. Additionally, the approach is advantageous in terms of step economy as it skips the prefunctionalization of styrenes to oxiranes, which has been inevitable in commonly used syntheses of 1,3-oxathiolane-2-thiones.