Zwitterionic-Salt-Catalyzed Site-Selective Monobromination of Arenes

A zwitterionic-salt-catalyzed electrophilic monobromination of arenes with high regioselectivity has been developed. Under mild reaction conditions, a wide range of monobrominated aromatic compounds can be obtained in excellent yields. The reaction can be operated using an extremely low catalyst loa...

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Bibliographic Details
Published in:Organic letters 2017-08, Vol.19 (16), p.4243-4246
Main Authors: Xiong, Xiaodong, Tan, Fei, Yeung, Ying-Yeung
Format: Article
Language:English
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Summary:A zwitterionic-salt-catalyzed electrophilic monobromination of arenes with high regioselectivity has been developed. Under mild reaction conditions, a wide range of monobrominated aromatic compounds can be obtained in excellent yields. The reaction can be operated using an extremely low catalyst loading (0.05 mol %) with the inexpensive brominating agent N-bromosuccinimide. The versatility of this catalytic protocol has been demonstrated by the scale-up reaction with a 0.01 mol % catalyst loading to provide the selectively halogenated compound in quantitative yield.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01899