Tetrahedron

Nucleophilic aromatic substitution reaction of nitroarenes with alkyl-or arylthio groups in dimethyl sulfoxide by means of cesium carbonate

A Kondoh, H Yorimitsu, K Oshima

Index: Kondoh, Azusa; Yorimitsu, Hideki; Oshima, Koichiro Tetrahedron, 2006 , vol. 62, # 10 p. 2357 - 2360

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Citation Number: 28

Abstract

Treatment of nitroarenes having electron-withdrawing groups at the ortho or para position with alkanethiol in the presence of cesium carbonate in dimethyl sulfoxide at 25° C leads to nucleophilic displacement of the nitro group with the alkylthio group. Cesium carbonate is superior to other bases such as potassium carbonate, sodium carbonate, and triethylamine. The cesium-mediated nucleophilic aromatic substitution reaction provides a mild yet ...