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Methyl Trifluoroacetate as a Methylation Reagent for N−H, O−H, and S−H Functionalities under Mild Conditions
Author(s) -
Zheng Xin,
Zeng Jiechun,
Xiong Mindong,
Huang Jiawei,
Li Cuiyan,
Zhou Rujin,
Xiao Duoduo
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900413
Subject(s) - reagent , chemistry , methylation , amide , functional group , organic chemistry , combinatorial chemistry , biochemistry , gene , polymer
A methylation reagent for compounds bearing N−H, O−H, and S−H functionalities was developed. Methyl trifluoroacetate (MTFA) was commonly considered as trifluoroacetylating reagent or trifluoromethylating reagent. In this work, we report the methylation behavior of MTFA under mild conditions with good functional group tolerance, allowing the transformation of a wide range of substrates, including N,H‐heteroaromatic compounds, phenolic compounds, carboxylic acids, thiophenols, secondary amides and imides, in high yields. This method was preliminarily applied to the chemoselective methylation of bifunctionalized secondary amide.