Copper powder-catalyzed regio- and stereoselective aminobromination of alpha,beta-unsaturated ketones with TsNH2 and NBS as nitrogen and halogen sources.
The regio- and stereoselective aminobromination of alpha,beta-unsaturated ketones catalyzed by copper powder has been established with 4-TsNH(2) and NBS as the nitrogen/bromine sources, respectively. This method provides an easy access for preparation of vicinal aminohalo derivatives in the presence of 1 mol % catalyst. Electron-rich alpha,beta-unsaturated ketones afforded the corresponding aminobrominated products in excellent yields (up to 99.8%), revealing that the addition has an electrophilic feature.
Chen
Zhan-Guo
ZG
School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an, 710062, People's Republic of China.
Wei
Jun-Fa
JF
Li
Run-Tao
RT
Shi
Xian-Ying
XY
Zhao
Peng-Fei
PF
D000475:Alkenes / Q000737:chemistry; D001557:Benzenesulfonates / Q000737:chemistry; D002384:Catalysis; D002599:Chalcone / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry; D014050:Toluene / Q000031:analogs & derivatives / Q000737:chemistry; D000096926:Benzenesulfonamides
D000475:Alkenes; D001557:Benzenesulfonates; D002599:Chalcone; D003300:Copper; D006842:Hydrocarbons, Brominated; D007659:Ketones; D013449:Sulfonamides; D014050:Toluene; C081297:4-nitrobenzenesulfonate; C025417:4-toluenesulfonamide; D000096926:Benzenesulfonamides