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Monofluoromethyl‐Substituted Sulfonium Ylides: Electrophilic Monofluoromethylating Reagents with Broad Substrate Scopes

Two electrophilic monofluoromethylating reagents, monofluoromethyl(phenyl)sulfonium bis(carbomethoxy)methylide (3 a) and monofluoromethyl(4‐nitrophenyl)sulfonium bis(carbomethoxy)methylide (3 b), and their reactions under mild conditions with a variety of nucleophiles, such as alcohols and malonate...

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Published in:Angewandte Chemie International Edition 2017-08, Vol.56 (33), p.9930-9934
Main Authors: Liu, Yafei, Lu, Long, Shen, Qilong
Format: Article
Language:English
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Summary:Two electrophilic monofluoromethylating reagents, monofluoromethyl(phenyl)sulfonium bis(carbomethoxy)methylide (3 a) and monofluoromethyl(4‐nitrophenyl)sulfonium bis(carbomethoxy)methylide (3 b), and their reactions under mild conditions with a variety of nucleophiles, such as alcohols and malonate derivatives, sulfonic and carboxylic acids, phenols, amides, and N heteroarenes, are described. Mechanistic studies with deuterated reagents [D2]3 a/[D2]3 b suggest that these monofluoromethylation reactions proceed through an electrophilic substitution pathway. Now in mono! Two sulfonium ylides (see scheme, R=H or NO2) were developed as effective reagents for the monofluoromethylation of a variety of nucleophiles, including alcohols and malonate derivatives, sulfonic and carboxylic acids, phenols, amides, and N heteroarenes, under mild conditions. Mechanistic studies suggest that these monofluoromethylation reactions proceed through an electrophilic substitution pathway.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201704175