Issue 11, 2012
From the journal:

Green Chemistry

Intermolecular photodecarboxylation of electron-deficient substrates by phthalimides in water: efficiency, selectivity and online monitoring†

Axel G. Griesbeck,*a   Nestor Nazarov,a   Jörg M. Neudörfla  and  Maria Heffena  

* Corresponding authors

a Department of Chemistry, Greinstr. 4, D-50939 Köln, Germany
E-mail: griesbeck@uni-koeln.de
Fax: +0049-221-4705057

Abstract

The intermolecular photodecarboxylation of arylacetic acids 3–5 in water by use of stoichiometric amounts of N-alkylated phthalimides 1a,b was investigated by NMR and online pH- and CO2-release sensing. Decreasing the electron donor capability of the arylacetic acids by 4-fluoro and trifluoromethyl substitution alters the efficiency of the photodecarboxylation and selectivity of the secondary reaction. A remarkable switch in reaction channel (A to B) was observed for perfluoropropionic acid.

Graphical abstract: Intermolecular photodecarboxylation of electron-deficient substrates by phthalimides in water: efficiency, selectivity and online monitoring

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Article information

DOI
https://doi.org/10.1039/C2GC36089F
Article type
Communication
Submitted
13 Jul 2012
Accepted
30 Aug 2012
First published
04 Sep 2012

Green Chem., 2012,14, 3004-3006

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Intermolecular photodecarboxylation of electron-deficient substrates by phthalimides in water: efficiency, selectivity and online monitoring

A. G. Griesbeck, N. Nazarov, J. M. Neudörfl and M. Heffen, Green Chem., 2012, 14, 3004 DOI: 10.1039/C2GC36089F

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