Organic Chemistry Portal



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:

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

DOI: 10.1021/acs.orglett.0c01928

see article for more reactions


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.

see article for more examples

proposed mechanism

Key Words

bromohydrins, NBS, multicomponent reactions, organocatalysis

ID: J54-Y2020