Organic Letters
Organic Letters
5 years ago

Zwitterionic-Salt-Catalyzed Site-Selective Monobromination of Arenes

Zwitterionic-Salt-Catalyzed Site-Selective Monobromination of Arenes
Xiaodong Xiong, Ying-Yeung Yeung, Fei Tan
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01899

DOI: 10.1021/acs.orglett.7b01899

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