ACS Catalysis p. 8083 - 8092 (2019)
Update date:2022-08-03
Topics:
Lam, Ying-Pong
Ng, Wing-Hin
Tan, Fei
Tse, Ying-Lung Steve
Wang, Xinyan
Yeung, Ying-Yeung
A class of zwitterionic organocatalysts based on an amide anion/iminium cation charge pair has been developed. The zwitterions are easily prepared by reacting aziridines with aminopyridines. They are catalytically applicable to transesterifications and dehydrative esterifications. Mechanistic studies reveal that the amide anion and iminium cation work synergistically in activating the reaction partners, with the iminium cationic moiety interacting with the carbonyl substrates through nonclassical hydrogen bonding. The reaction can be applied to large-scale synthesis of biodiesel under mild conditions.
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