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Synthesis 2007(2): 243-250
DOI: 10.1055/s-2006-958947
DOI: 10.1055/s-2006-958947
PAPER
© Georg Thieme Verlag Stuttgart · New York
Palladium-Catalyzed N-Arylation Reactions with Aziridine and Azetidine
Further Information
Received
3 August 2006
Publication Date:
14 December 2006 (online)
Publication History
Publication Date:
14 December 2006 (online)
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Abstract
Studies on the viability of palladium-catalyzed cross-coupling reactions of aryl- or hetaryl bromides with the parent aziridine or azetidine showed that a wide range of N-arylaziridines and N-arylazetidines are accessible by this method. Ring cleavage of the N-arylaziridines or -azetidines thus produced does not occur under the applied reaction conditions. The synthetic utility of the method is illustrated by examples of double N-arylations with either aziridine or azetidine.
Key words
aziridines - azetidines - N-arylations - cross-coupling - palladium
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References
No efforts were undertaken to optimize the reaction regarding the amount of aziridine, because of its high volatility (bp 57 °C/780 Torr).