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Synthesis 2011(22): 3680-3686
DOI: 10.1055/s-0030-1260245
DOI: 10.1055/s-0030-1260245
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Potassium Carbonate Catalyzed Regioselective Aminohalogenation of β-Nitrostyrenes by Using Benzyl Carbamate/N-Chlorosuccinimide as a New Nitrogen/Chlorine Source
Further Information
Publication History
Received
29 July 2011
Publication Date:
29 September 2011 (online)


Abstract
A combination of benzyl carbamate and N-chlorosuccinimide was developed as a new system for aminohalogenation of β-nitrostyrenes catalyzed by potassium carbonate in dichloromethane at room temperature. The reaction tolerates a wide range of substituents on the β-nitrostyrene, and proceeds smoothly in good-to-excellent chemical yields (77-99%). The new system shows a high efficiency and it markedly shortens the reaction time for aminochlorination. N,N-Dichlorobenzyl carbamate was also found to be a highly efficient source of both nitrogen and chlorine for the aminohalogenation reaction.
Key words
aminations - chlorinations - alkenes - carbamates - amides
- Supporting Information for this article is available online:
- Supporting Information
- Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0019th:
- Primary Data