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Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion

An associative electron upconversion is proposed as a key step determining the selectivity of thiol–yne coupling. The developed synthetic approach provided an efficient tool to access a comprehensive range of products – four types of vinyl sulfides were prepared in high yields and selectivity. We re...

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Autores principales: Burykina, Julia V., Shlapakov, Nikita S., Gordeev, Evgeniy G., König, Burkhard, Ananikov, Valentine P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162103/
https://www.ncbi.nlm.nih.gov/pubmed/34094267
http://dx.doi.org/10.1039/d0sc01939a
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author Burykina, Julia V.
Shlapakov, Nikita S.
Gordeev, Evgeniy G.
König, Burkhard
Ananikov, Valentine P.
author_facet Burykina, Julia V.
Shlapakov, Nikita S.
Gordeev, Evgeniy G.
König, Burkhard
Ananikov, Valentine P.
author_sort Burykina, Julia V.
collection PubMed
description An associative electron upconversion is proposed as a key step determining the selectivity of thiol–yne coupling. The developed synthetic approach provided an efficient tool to access a comprehensive range of products – four types of vinyl sulfides were prepared in high yields and selectivity. We report practically important transition-metal-free regioselective thiol–yne addition and formation of the demanding Markovnikov-type product by a radical photoredox process. The photochemical process was directly monitored by mass-spectrometry in a specially designed ESI-MS device with green laser excitation in the spray chamber. The proposed reaction mechanism is supported by experiments and DFT calculations.
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spelling pubmed-81621032021-06-04 Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion Burykina, Julia V. Shlapakov, Nikita S. Gordeev, Evgeniy G. König, Burkhard Ananikov, Valentine P. Chem Sci Chemistry An associative electron upconversion is proposed as a key step determining the selectivity of thiol–yne coupling. The developed synthetic approach provided an efficient tool to access a comprehensive range of products – four types of vinyl sulfides were prepared in high yields and selectivity. We report practically important transition-metal-free regioselective thiol–yne addition and formation of the demanding Markovnikov-type product by a radical photoredox process. The photochemical process was directly monitored by mass-spectrometry in a specially designed ESI-MS device with green laser excitation in the spray chamber. The proposed reaction mechanism is supported by experiments and DFT calculations. The Royal Society of Chemistry 2020-07-23 /pmc/articles/PMC8162103/ /pubmed/34094267 http://dx.doi.org/10.1039/d0sc01939a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Burykina, Julia V.
Shlapakov, Nikita S.
Gordeev, Evgeniy G.
König, Burkhard
Ananikov, Valentine P.
Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion
title Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion
title_full Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion
title_fullStr Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion
title_full_unstemmed Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion
title_short Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion
title_sort selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162103/
https://www.ncbi.nlm.nih.gov/pubmed/34094267
http://dx.doi.org/10.1039/d0sc01939a
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