Approach to Vicinal t-Boc-amino Dibromides via Catalytic Aminobromination of Nitrostyrenes without Using Chromatography and Recrystallization

作者：Sun Hao; Han Jianlin; Kattamuri Padmanabha V; Pan Yi^*; Li Guigen

来源：Journal of Organic Chemistry, 2013, 78(3): 1171-1175.

DOI：10.1021/jo302727v

A 1.0 mol % amount of K3PO4 center dot 3H(2)O was found to catalyze aminohalogenation reaction of nitrostyrenes with N,N-dibromo-tert-butylcarbamate (t-Boc-NBr2) in a dichloroethane system. Good to excellent yields and complete regioselectivity have been achieved by taking advantage of the GAP workup without using traditional purification techniques such as column chromatography and recrystallization. A new mechanism is proposed involving radical and ionic catalytic cycles and an intramolecular migration.

• 出版日期2013-2-1
• 单位南京大学