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Zwitterion-Catalyzed Intermolecular Bromoesterifications

Wing-Hin Ng, Rong-Bin Hu, Ying-Pong Lam and Ying-Yeung Yeung*

*Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China, Email: yyyeungcuhk.edu.hk

W.-H. Ng, R.-B. Hu, Y.-P. Lam, Y.-Y. Yeung, Org. Lett., 2020, 22, 5567-5571.

DOI: 10.1021/acs.orglett.0c01928 (free Supporting Information)



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Abstract

A zwitterion-catalyzed intermolecular bromoesterification of alkenes works with acid and olefin in an equimolar ratio. Mechanistic study revealed that the charge pair in the zwitterion works synergistically in activating both NBS and carboxylic acid.

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proposed mechanism



Key Words

bromohydrins, NBS, multicomponent reactions, organocatalysis


ID: J54-Y2020