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

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
Format: Artikel
Sprache:eng
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Alkenes
Benzamide
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Nitrogen
Room temperature
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container_end_page 1952
container_issue 9
container_start_page 1946
container_title Science China. Chemistry
container_volume 53
creator Zhi, SanJun
Mei, HaiBo
Zhang, GuangQian
Sun, Hao
Han, JianLin
Li, GuiGen
Pan, Yi
description 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.
doi_str_mv 10.1007/s11426-010-4001-4
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subjects Alkenes
Benzamide
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Nitrogen
Room temperature
title The combination of benzamides/NCS as nitrogen/halogen sources for aminohalogenation of β-nitrostyrenes resulting in dichlorinated haloamides
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