Issue 11, 2012

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

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

Supplementary files

Additions and corrections

Article information

Article type
Communication
Submitted
13 Jul 2012
Accepted
30 Aug 2012
First published
04 Sep 2012

Green Chem., 2012,14, 3004-3006

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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