K3PO4-catalyzed regiospecific aminobromination of beta-nitrostyrene derivatives with N-bromoacetamide as aminobrominating agent.
A very simple, efficient, and regiospecific protocol for aminobromination of a wide scope of beta-nitrostyrene derivatives with N-bromoacetamide (NBA) as nitrogen/bromine sources has been developed by using K(3)PO(4) as catalyst. The reaction proceeded smoothly and cleanly to give the bromoamines in good to excellent yields (78-99%) within 24 h in CH(2)Cl(2) at room temperature without protection of inert gases. A possible mechanism involving a nucleophilic conjugate addition was proposed.
Chen
Zhan-Guo
ZG
School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an, 710062, People's Republic of China.
Wang
Yun
Y
Wei
Jun-Fa
JF
Zhao
Peng-Fei
PF
Shi
Xian-Ying
XY
D000081:Acetamides / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008752:Methylene Chloride / Q000737:chemistry; D015394:Molecular Structure; D010710:Phosphates / Q000737:chemistry*; D017680:Potassium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*
D000081:Acetamides; D000588:Amines; D010710:Phosphates; D017680:Potassium Compounds; D013343:Styrenes; C016272:N-bromoacetamide; C011955:beta-nitrostyrene; D008752:Methylene Chloride; C013216:potassium phosphate; D001966:Bromine