Intermolecular Photocatalytic Chemo‐, Stereo‐ and Regioselective Thiol–Yne–Ene Coupling Reaction
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.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
Intermolecular Photocatalytic Chemo‐, Stereo‐ and Regioselective Thiol–Yne–Ene Coupling Reaction ; day:02 ; month:03 ; year:2022 ; extent:1
Angewandte Chemie ; (02.03.2022) (gesamt 1)
- Urheber
-
Burykina, Julia V.
Kobelev, Andrey D.
Shlapakov, Nikita S.
Kostyukovich, Alexander Yu.
Fakhrutdinov, Artem N.
König, Burkhard
Ananikov, Valentine P.
- DOI
-
10.1002/ange.202116888
- URN
-
urn:nbn:de:101:1-2022030314033420061586
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
15.08.2025, 07:32 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Burykina, Julia V.
- Kobelev, Andrey D.
- Shlapakov, Nikita S.
- Kostyukovich, Alexander Yu.
- Fakhrutdinov, Artem N.
- König, Burkhard
- Ananikov, Valentine P.
Ähnliche Objekte (12)
Intermolecular Photocatalytic Chemo‐, Stereo‐ and Regioselective Thiol–Yne–Ene Coupling Reaction
Functional Graphene by Thiol‐ene Click Chemistry
Tunable and Magnetic Thiol–ene Micropillar Arrays
Radical‐Mediated Thiol‐Ene Strategy: Photoactivation of Thiol‐Containing Drugs in Cancer Cells
Radical‐Mediated Thiol‐Ene Strategy: Photoactivation of Thiol‐Containing Drugs in Cancer Cells
Investigations of thiol-modified phenol derivatives for the use in thiol–ene photopolymerizations
Purple‐Light Promoted Thiol‐ene Reaction of Alkenes
Functionalization of Polymer Nanoparticles by Thiol-Ene Addition
Polyfunctionalizations of N-heterocycles via chemo- and regioselective metalations
Investigation of the network inhomogeneity of thiol-ene organogels
Investigation of the network inhomogeneity of thiol-ene organogels
Highly Tunable Thiol‐Ene Photoresins for Volumetric Additive Manufacturing
Intermolecular Photocatalytic Chemo‐, Stereo‐ and Regioselective Thiol–Yne–Ene Coupling Reaction
Functional Graphene by Thiol‐ene Click Chemistry
Tunable and Magnetic Thiol–ene Micropillar Arrays
Radical‐Mediated Thiol‐Ene Strategy: Photoactivation of Thiol‐Containing Drugs in Cancer Cells
Radical‐Mediated Thiol‐Ene Strategy: Photoactivation of Thiol‐Containing Drugs in Cancer Cells
Investigations of thiol-modified phenol derivatives for the use in thiol–ene photopolymerizations
Purple‐Light Promoted Thiol‐ene Reaction of Alkenes
Functionalization of Polymer Nanoparticles by Thiol-Ene Addition
Polyfunctionalizations of N-heterocycles via chemo- and regioselective metalations
Investigation of the network inhomogeneity of thiol-ene organogels
Investigation of the network inhomogeneity of thiol-ene organogels
Highly Tunable Thiol‐Ene Photoresins for Volumetric Additive Manufacturing
Intermolecular Photocatalytic Chemo‐, Stereo‐ and Regioselective Thiol–Yne–Ene Coupling Reaction
Functional Graphene by Thiol‐ene Click Chemistry
Tunable and Magnetic Thiol–ene Micropillar Arrays
Radical‐Mediated Thiol‐Ene Strategy: Photoactivation of Thiol‐Containing Drugs in Cancer Cells
Radical‐Mediated Thiol‐Ene Strategy: Photoactivation of Thiol‐Containing Drugs in Cancer Cells
Investigations of thiol-modified phenol derivatives for the use in thiol–ene photopolymerizations
Purple‐Light Promoted Thiol‐ene Reaction of Alkenes
Functionalization of Polymer Nanoparticles by Thiol-Ene Addition
Polyfunctionalizations of N-heterocycles via chemo- and regioselective metalations
Investigation of the network inhomogeneity of thiol-ene organogels
Investigation of the network inhomogeneity of thiol-ene organogels