A one-pot strategy for the synthesis of α-bromo enaminones is reported. The reactions proceed via the p-toluenesulfonic acid monohydrate (TsOH • H 2 O) catalyzed reactions of 3-bromopropenals with anilines in dimethyl sulfoxide (DMSO) and does not require an external brominating agent. The chemoselective 1,2addition was accomplished by employing aniline with a sterically hindered electron-withdrawing group attached at the ortho-position. In addition, the reactions involving other aniline derivatives as nucleophiles have resulted in minor yields of 1,4-addition product. The 3-bromopropenals showed a diverse range of reactivities with aniline derivatives.
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