Photocatalyzed Carbon−Carbon Bond Formation Between Glycerol and Electron‐Deficient Olefins
Abstract: Glycerol is produced in large quantities as a co‐product in the manufacturing of biodiesel and has received relatively little attention as a substrate for carbon−carbon bond‐forming reactions. In this work, the photocatalyzed reaction between glycerol and electron‐deficient olefins is investigated to regioselectively insert an alkyl group at C2 in the triol. The results show that the transformation is highly dependent on the nature of the photocatalyst and the olefin. In the presence of an iridium catalyst and quinuclidine, glycerol can be coupled at C2 with sterically unhindered acrylates. In the presence of tetrabutylammonium decatungstate, glycerol can be reacted with fumaronitrile, N‐methyl maleimide, methyl acrylate and itaconic anhydride where the latter two substrates require the additional presence of potassium persulfate as an oxidant. These findings give rise to several new carbon−carbon bond‐forming reactions with glycerol that allow the triol to be converted into more elaborate structures.
- Location
-
Deutsche Nationalbibliothek Frankfurt am Main
- Extent
-
Online-Ressource
- Language
-
Englisch
- Bibliographic citation
-
Photocatalyzed Carbon−Carbon Bond Formation Between Glycerol and Electron‐Deficient Olefins ; day:02 ; month:11 ; year:2023 ; extent:6
ChemCatChem ; (02.11.2023) (gesamt 6)
- Creator
-
El‐Chami, Kassem
Madsen, Robert
- DOI
-
10.1002/cctc.202301143
- URN
-
urn:nbn:de:101:1-2023110314145815473519
- Rights
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
- 14.08.2025, 10:50 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- El‐Chami, Kassem
- Madsen, Robert
Other Objects (12)
Decatungstate‐Catalyzed Carbon‐Carbon Bond Formation Between Furfural and Electron‐Deficient Olefins
Iron-catalyzed carbon-carbon bond activation
Photocatalytic activation for carbon-carbon bond formations
Stereoselective reactions of carbon-carbon double bonds
Catalytic hydroarylation of carbon-carbon multiple bonds
Photoinduced carbon-selenium bond formation and carbon-boron bond formation reaction
Phosphorus-carbon double bonds
Carbon-Hydrogen bond activation
Mechanisms of reactions at carbon-carbon double bonds
Catalytic carbonylative functionalization of multiple carbon-carbon bonds
Palladium-catalyzed carbonylation of unsaturated carbon-carbon bonds
Photocatalytic Carbon – Carbon Bond Formations with Visible Light
Decatungstate‐Catalyzed Carbon‐Carbon Bond Formation Between Furfural and Electron‐Deficient Olefins
Iron-catalyzed carbon-carbon bond activation
Photocatalytic activation for carbon-carbon bond formations
Stereoselective reactions of carbon-carbon double bonds
Catalytic hydroarylation of carbon-carbon multiple bonds
Photoinduced carbon-selenium bond formation and carbon-boron bond formation reaction
Phosphorus-carbon double bonds
Carbon-Hydrogen bond activation
Mechanisms of reactions at carbon-carbon double bonds
Catalytic carbonylative functionalization of multiple carbon-carbon bonds
Palladium-catalyzed carbonylation of unsaturated carbon-carbon bonds
Photocatalytic Carbon – Carbon Bond Formations with Visible Light
Decatungstate‐Catalyzed Carbon‐Carbon Bond Formation Between Furfural and Electron‐Deficient Olefins
Iron-catalyzed carbon-carbon bond activation
Photocatalytic activation for carbon-carbon bond formations
Stereoselective reactions of carbon-carbon double bonds
Catalytic hydroarylation of carbon-carbon multiple bonds
Photoinduced carbon-selenium bond formation and carbon-boron bond formation reaction
Phosphorus-carbon double bonds
Carbon-Hydrogen bond activation
Mechanisms of reactions at carbon-carbon double bonds
Catalytic carbonylative functionalization of multiple carbon-carbon bonds
Palladium-catalyzed carbonylation of unsaturated carbon-carbon bonds