Influence of solvent, electron acceptors and arenes on photochemical decarboxylation of free carboxylic acids via single electron transfer (SET).

Yasuharu Yoshimi, Shota Hayashi, Keisuke Nishikawa, Yoshiki Haga, Kousuke Maeda, Toshio Morita, Tatsuya Itou, Yutaka Okada, Nobuyuki Ichinose, Minoru Hatanaka

Index: Molecules 15(4) , 2623-30, (2010)

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Abstract

Single electron transfer (SET)-photochemical decarboxylation of free carboxylic acids was performed in a polar solvent using several arenes such as phenanthrene, naphthalene, 1-methylnaphthalene, biphenyl, triphenylene, and chrysene in the presence of various electron acceptors such as 1,2-, 1,3-, and 1,4-dicyanobenzenes, methyl 4-cyanobenzoate, and 1,4-dicyanonaphthalene. The decarboxylation reaction was influenced by the arenes, electron acceptors, and solvent. The best result was achieved by the photoreaction using biphenyl and 1,4-dicyanonaphthalene in aqueous acetonitrile.