Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Zalesskiy, Sergey S., Shlapakov, Nikita S., Ananikov, Valentine P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
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
_version_ 1782515679349440512
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
title_full Visible light mediated metal-free thiol–yne click reaction
title_fullStr Visible light mediated metal-free thiol–yne click reaction
title_full_unstemmed Visible light mediated metal-free thiol–yne click reaction
title_short Visible light mediated metal-free thiol–yne click reaction
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