Metal-free, visible-light-mediated, decarboxylative alkylation of biomass-derived compounds

Schwarz, Johanna and Koenig, Burkhard (2016) Metal-free, visible-light-mediated, decarboxylative alkylation of biomass-derived compounds. GREEN CHEMISTRY, 18 (17). pp. 4743-4749. ISSN 1463-9262, 1463-9270

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Abstract

This work describes a mild, environmentally friendly method to activate natural carboxylic acids for decarboxylative alkylation. After esterification of biomass-derived acids to N-(acyloxy)phthalimides, the active esters are cleaved reductively by photocatalysis to give alkyl radicals, which undergo C-C bond formation with electron-deficient alkenes. This reaction is catalyzed by the organic dye eosin gamma and green light (535 nm) and the scope of acids includes abundant amino acids, alpha-oxy acids and fatty acids which are available from renewable resources.

Item Type: Article
Uncontrolled Keywords: ALPHA-AMINO-ACIDS; PHOTOCATALYTIC HYDROGEN-PRODUCTION; ELECTRON-DEFICIENT ALKENES; ALIPHATIC CARBOXYLIC-ACIDS; PHOTOREDOX CATALYSIS; NICKEL CATALYSIS; EOSIN-Y; HETEROGENEOUS PHOTOCATALYSIS; MERGING PHOTOREDOX; COUPLING REACTIONS;
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie
Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 Mar 2019 09:28
Last Modified: 14 Mar 2019 09:28
URI: https://pred.uni-regensburg.de/id/eprint/2661

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