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  • Copper powder-catalyzed regio- and stereoselective aminobromination of alpha,beta-unsaturated ketones with TsNH2 and NBS as nitrogen and halogen sources.

Copper powder-catalyzed regio- and stereoselective aminobromination of alpha,beta-unsaturated ketones with TsNH2 and NBS as nitrogen and halogen sources.

The Journal of organic chemistry (2008-12-26)
Zhan-Guo Chen, Jun-Fa Wei, Run-Tao Li, Xian-Ying Shi, Peng-Fei Zhao
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
p-Toluenesulfonamide, ReagentPlus®, ≥99%
Sigma-Aldrich
p-Toluenesulfonamide, reagent grade, 98%