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Issue 11, 2016
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Visible light mediated metal-free thiol–yne click reaction

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Abstract

The carbon–sulfur bond formation reaction is of paramount importance for functionalized materials design, as well as for biochemical applications. The use of expensive metal-based catalysts and the consequent contamination with trace metal impurities are challenging drawbacks of the existing methodologies. Here, we describe the first environmentally friendly metal-free photoredox pathway to the thiol–yne click reaction. Using Eosin Y as a cheap and readily available catalyst, C–S coupling products were obtained in high yields (up to 91%) and excellent selectivity (up to 60 : 1). A 3D-printed photoreactor was developed to create arrays of parallel reactions with temperature stabilization to improve the performance of the catalytic system.

Graphical abstract: Visible light mediated metal-free thiol–yne click reaction

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Supplementary files

Article information


Submitted
14 May 2016
Accepted
08 Jul 2016
First published
12 Jul 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 6740-6745
Article type
Edge Article

Visible light mediated metal-free thiol–yne click reaction

S. S. Zalesskiy, N. S. Shlapakov and V. P. Ananikov, Chem. Sci., 2016, 7, 6740
DOI: 10.1039/C6SC02132H

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

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    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
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    [Original citation] - Published by The Royal Society of Chemistry.

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