Angewandte Chemie - International Edition, volume 61, issue 17
Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-yne-ene Coupling Reaction.
Publication type: Journal Article
Publication date: 2022-03-02
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
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.
Top-30
Journals
|
1
2
3
|
|
|
Organic Chemistry Frontiers
3 publications, 9.38%
|
|
|
Organic and Biomolecular Chemistry
2 publications, 6.25%
|
|
|
Chemical Science
2 publications, 6.25%
|
|
|
Advanced Synthesis and Catalysis
2 publications, 6.25%
|
|
|
Russian Journal of Organic Chemistry
2 publications, 6.25%
|
|
|
Angewandte Chemie - International Edition
2 publications, 6.25%
|
|
|
Angewandte Chemie
2 publications, 6.25%
|
|
|
Green Chemistry
2 publications, 6.25%
|
|
|
Журнал органической химии
2 publications, 6.25%
|
|
|
European Polymer Journal
1 publication, 3.13%
|
|
|
ChemPhotoChem
1 publication, 3.13%
|
|
|
ChemCatChem
1 publication, 3.13%
|
|
|
Chemistry - A European Journal
1 publication, 3.13%
|
|
|
Organic Process Research and Development
1 publication, 3.13%
|
|
|
Molecules
1 publication, 3.13%
|
|
|
Science China Chemistry
1 publication, 3.13%
|
|
|
Journal of Organic Chemistry
1 publication, 3.13%
|
|
|
Chemical Communications
1 publication, 3.13%
|
|
|
Journal of the Taiwan Institute of Chemical Engineers
1 publication, 3.13%
|
|
|
ChemPlusChem
1 publication, 3.13%
|
|
|
Synlett
1 publication, 3.13%
|
|
|
European Journal of Organic Chemistry
1 publication, 3.13%
|
|
|
1
2
3
|
Publishers
|
2
4
6
8
10
12
|
|
|
Wiley
11 publications, 34.38%
|
|
|
Royal Society of Chemistry (RSC)
10 publications, 31.25%
|
|
|
Elsevier
2 publications, 6.25%
|
|
|
American Chemical Society (ACS)
2 publications, 6.25%
|
|
|
Pleiades Publishing
2 publications, 6.25%
|
|
|
Akademizdatcenter Nauka
2 publications, 6.25%
|
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 3.13%
|
|
|
Springer Nature
1 publication, 3.13%
|
|
|
Thieme
1 publication, 3.13%
|
|
|
2
4
6
8
10
12
|
- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
Cite this
GOST |
RIS |
BibTex
Cite this
GOST
Copy
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.
GOST all authors (up to 50)
Copy
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.
Cite this
RIS
Copy
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 - Fakhrutdinov, Artem N.
AU - Burykina, Julia V.
AU - Kobelev, Andrey D
AU - Shlapakov, Nikita S
AU - Kostyukovich, Alexander Yu
AU - König, Burkhard
AU - Ananikov, Valentine P.
PY - 2022
DA - 2022/03/02
PB - Wiley
IS - 17
VL - 61
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex
Copy
@article{2022_Burykina,
author = {Artem N. Fakhrutdinov and Julia V. Burykina and Andrey D Kobelev and Nikita S Shlapakov and Alexander Yu Kostyukovich 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}
}