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Issue 37, 2020
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Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion

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Abstract

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.

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

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Supplementary files

Article information


Submitted
05 Apr 2020
Accepted
22 Jul 2020
First published
23 Jul 2020

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

Chem. Sci., 2020,11, 10061-10070
Article type
Edge Article

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

J. V. Burykina, N. S. Shlapakov, E. G. Gordeev, B. König and V. P. Ananikov, Chem. Sci., 2020, 11, 10061
DOI: 10.1039/D0SC01939A

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