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Issue 17, 2016
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Metal-free, visible-light-mediated, decarboxylative alkylation of biomass-derived compounds

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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 Y and green light (535 nm) and the scope of acids includes abundant amino acids, α-oxy acids and fatty acids which are available from renewable resources.

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

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Supplementary files

Article information


Submitted
18 Apr 2016
Accepted
25 May 2016
First published
26 May 2016

This article is Open Access

Green Chem., 2016,18, 4743-4749
Article type
Paper

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

J. Schwarz and B. König, Green Chem., 2016, 18, 4743
DOI: 10.1039/C6GC01101B

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