Abstract
The combination of benzamide and NCS was found to be an efficient nitrogen/halogen source for aminohalogenation of β-nitrostyrenes. The reaction was convenient to carry out by using 4-dimethylaminopyridine as the catalyst, resulting in vicinal dichlorinated haloamino nitroalkanes with opposite regiochemistry to that generated from other electron-deficient olefins observed previously. The reaction proceeded smoothly at room temperature with good yields and excellent regioselectivities. A mechanism involving a chloronium intermediate was proposed to explain the resulting regiochemistry. The current system explored a new type of nitrogen sources for aminohalogenation of functionalized olefins.
Original language | English |
---|---|
Pages (from-to) | 1946-1952 |
Number of pages | 7 |
Journal | Science China Chemistry |
Volume | 53 |
Issue number | 9 |
DOIs | |
State | Published - Sep 2010 |
Keywords
- DMAP
- aminohalogenation
- benzamide
- haloamides
- β-nitrostyrenes