Burykina, Julia and Kobelev, Andrey D. and Shlapakov, Nikita S. and Kostyukovich, Alexander Yu and Fakhrutdinov, Artem N. and Koenig, Burkhard and Ananikov, Valentine P. (2022) Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-Yne-Ene Coupling Reaction. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 61 (17): e202116888. ISSN 1433-7851, 1521-3773
Full text not available from this repository. (Request a copy)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 sigma-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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | VISIBLE-LIGHT; CLICK CHEMISTRY; DIELS-ALDER; STEREOSELECTIVE-SYNTHESIS; FLUORINE; ALKYNES; CARBOMETALATION; POLYMERIZATION; CATALYSIS; ALKENES; Multicomponent Reactions; Photocatalysis; Reaction Mechanisms; Thiol-Yne-Ene; Visible Light |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 15 Feb 2024 13:44 |
| Last Modified: | 15 Feb 2024 13:44 |
| URI: | https://pred.uni-regensburg.de/id/eprint/57705 |
Actions (login required)
 |
View Item |
