The combination of benzamides/NCS as nitrogen/halogen sources for aminohalogenation of β-nitrostyrenes resulting in dichlorinated haloamides

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 regio...

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Veröffentlicht in:Science China. Chemistry 2010-09, Vol.53 (9), p.1946-1952
Hauptverfasser: Zhi, SanJun, Mei, HaiBo, Zhang, GuangQian, Sun, Hao, Han, JianLin, Li, GuiGen, Pan, Yi
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Sprache:eng
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Zusammenfassung: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.
ISSN:1674-7291
1869-1870
DOI:10.1007/s11426-010-4001-4