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Making Carbonyls of Amides Nucleophilic and Hydroxyls of Alcohols Electrophilic Mediated by SO2F2 for Synthesis of Esters from Amides

Wan-Yin Fang, Gao-Feng Zha and Hua-Li Qin*

*School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, 205 Luoshi Road, Wuhan 430070, P. R. China, Email: qinhualiwhut.edu.cn

W.-Y. Fang, G.-F. Zha, H.-L. Qin, Org. Lett., 2019, 21, 8657-8661.

DOI: 10.1021/acs.orglett.9b03274 (free Supporting Information)


Abstract

Sulfuryl fluoride activates the carbonyl groups of amides as nucleophiles while the activated hydroxyl groups of alcohols act as electrophiles. The amide C-N bonds could be easily cleaved to form the ester C-O bonds at room temperature without using transition metals. The reaction offers broad substrate scope and excellent functional group compatibility.


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proposed mechanism



Key Words

esters, alkylation


ID: J54-Y2019