Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-yne-ene Coupling Reaction.
Publication type: Journal Article
Publication date: 2022-03-02
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
35147284
General Chemistry
Catalysis
Abstract
The first example of an intermolecular thiol–yne–ene coupling reaction is reported for the one‐pot construction of C−S and C−C bonds. Thiol–yne–ene coupling opens a new dimension in building molecular complexity to access densely functionalized products. The employment of Eosin Y/DBU/MeOH photocatalytic system suppresses hydrogen atom transfer (HAT) and associative reductant upconversion (via C−S three‐electron σ‐bond formation). Investigation of the reaction mechanism by combining online ESI‐UHRMS, EPR spectroscopy, isotope labeling, determination of quantum yield, cyclic voltammetry, Stern–Volmer measurements and computational modeling revealed a unique photoredox cycle with four radical‐involving stages. As a result, previously unavailable products of the thiol–yne–ene reaction were obtained in good yields with high selectivity. They can serve as stable precursors for synthesizing synthetically demanding activated 1,3‐dienes.
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41
Total citations:
41
Citations from 2024:
23
(56%)
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Burykina J. V. et al. Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-yne-ene Coupling Reaction. // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 17.
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Burykina J. V., Kobelev A. D., Shlapakov N. S., Kostyukovich A. Yu., Fakhrutdinov A. N., König B., Ananikov V. P. Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-yne-ene Coupling Reaction. // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 17.
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TY - JOUR
DO - 10.1002/anie.202116888
UR - https://doi.org/10.1002/anie.202116888
TI - Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-yne-ene Coupling Reaction.
T2 - Angewandte Chemie - International Edition
AU - Burykina, Julia V.
AU - Kobelev, Andrey D
AU - Shlapakov, Nikita S
AU - Kostyukovich, Alexander Yu
AU - Fakhrutdinov, Artem N.
AU - König, Burkhard
AU - Ananikov, Valentine P.
PY - 2022
DA - 2022/03/02
PB - Wiley
IS - 17
VL - 61
PMID - 35147284
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2022_Burykina,
author = {Julia V. Burykina and Andrey D Kobelev and Nikita S Shlapakov and Alexander Yu Kostyukovich and Artem N. Fakhrutdinov and Burkhard König and Valentine P. Ananikov},
title = {Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-yne-ene Coupling Reaction.},
journal = {Angewandte Chemie - International Edition},
year = {2022},
volume = {61},
publisher = {Wiley},
month = {mar},
url = {https://doi.org/10.1002/anie.202116888},
number = {17},
doi = {10.1002/anie.202116888}
}