Potassium Carbonate Catalyzed Regioselective Aminohalogenation of β-Nitrostyrenes by Using Benzyl Carbamate/N-Chlorosuccinimide as a New Nitrogen/Chlorine Source

Xiaoyun Ji, Haibo Mei, Yu Qian, Jianlin Han, Guigen Li & Yi Pan
A combination of benzyl carbamate and N-chlorosuccinimide was developed as a new system for aminohalogenation of β-nitrostyrenes catalyzed by potassium carbonate in dichloromethane at room temperature. The reaction tolerates a wide range of substituents on the β-nitrostyrene, and proceeds smoothly in good-to-excellent­ chemical yields (77-99%). The new system shows a high efficiency and it markedly shortens the reaction time for aminochlorination. N,N-Dichlorobenzyl carbamate was also found to be a highly efficient source of both nitrogen...