K₃PO₄-catalyzed regiospecific bromoamidation of β, β-dicyanostyrene derivatives with N-bromoacetamide(NBA)

Abstract

An efficient method for the bromoamidation of β,β-dicyanostyrene derivatives with N-bromoacetamide (NBA) was developed. This protocol provides a convenient process to convert β,β-dicyanostyrene derivatives into the vicinal haloamines in excellent yields(up to 99%) at room temperature in the presence of anhydrous K₃PO₄ as a catalyst without the protection of the inert gaseous in CH₂Cl₂. A total of 11 examples were investigated and all the products showed the regionspecific feature. Based on the observation of different activities for the different substrates involving the electron-rich or electron-deficient β,β-dicyanostyrenes, a possible Michael addition mechanism was proposed.

Keywords

Bromoamidation / β,β-Dicyanostyrene derivative / N-Bromoacetamide / Regiospecificity / Catalytic reaction

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