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Visible light mediated metal-free thiol–yne click reaction
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 methodo...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5355861/ https://www.ncbi.nlm.nih.gov/pubmed/28451118 http://dx.doi.org/10.1039/c6sc02132h |
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author | Zalesskiy, Sergey S. Shlapakov, Nikita S. Ananikov, Valentine P. |
author_facet | Zalesskiy, Sergey S. Shlapakov, Nikita S. Ananikov, Valentine P. |
author_sort | Zalesskiy, Sergey S. |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-5355861 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-53558612017-04-27 Visible light mediated metal-free thiol–yne click reaction Zalesskiy, Sergey S. Shlapakov, Nikita S. Ananikov, Valentine P. Chem Sci Chemistry 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. Royal Society of Chemistry 2016-11-01 2016-07-12 /pmc/articles/PMC5355861/ /pubmed/28451118 http://dx.doi.org/10.1039/c6sc02132h Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Chemistry Zalesskiy, Sergey S. Shlapakov, Nikita S. Ananikov, Valentine P. Visible light mediated metal-free thiol–yne click reaction |
title | Visible light mediated metal-free thiol–yne click reaction
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title_full | Visible light mediated metal-free thiol–yne click reaction
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title_fullStr | Visible light mediated metal-free thiol–yne click reaction
|
title_full_unstemmed | Visible light mediated metal-free thiol–yne click reaction
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title_short | Visible light mediated metal-free thiol–yne click reaction
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title_sort | visible light mediated metal-free thiol–yne click reaction |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5355861/ https://www.ncbi.nlm.nih.gov/pubmed/28451118 http://dx.doi.org/10.1039/c6sc02132h |
work_keys_str_mv | AT zalesskiysergeys visiblelightmediatedmetalfreethiolyneclickreaction AT shlapakovnikitas visiblelightmediatedmetalfreethiolyneclickreaction AT ananikovvalentinep visiblelightmediatedmetalfreethiolyneclickreaction |