Tetrahedron Letters

Superelectrophilic bromination of deactivated aromatic rings with tribromoisocyanuric acid—an experimental and DFT study

LS de Almeida, PM Esteves, MCS de Mattos

Index: de Almeida, Leonardo S.; Esteves, Pierre M.; de Mattos, Marcio C.S. Tetrahedron Letters, 2009 , vol. 50, # 25 p. 3001 - 3004

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Citation Number: 30

Abstract

The reaction of deactivated arenes with tribromoisocyanuric acid (TBCA) in 98% H2SO4 produced bromoarenes in good yields. The acidity of the medium controls the strength of the brominating agent and the amount of polybrominated products. DFT calculations at B3LYP/6- 311++ G∗∗ level showed that the protonated TBCA (a superelectrophilic species) can easily transfer Br+ to deactivated arenes, in order to decrease internal charge–charge ...