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Monofluoromethyl‐Substituted Sulfonium Ylides: Electrophilic Monofluoromethylating Reagents with Broad Substrate Scopes
Author(s) -
Liu Yafei,
Lu Long,
Shen Qilong
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201704175
Subject(s) - sulfonium , electrophile , chemistry , reagent , nucleophile , malonate , electrophilic substitution , substitution reaction , organic chemistry , nucleophilic substitution , medicinal chemistry , combinatorial chemistry , salt (chemistry) , catalysis
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 [D 2 ] 3 a /[D 2 ] 3 b suggest that these monofluoromethylation reactions proceed through an electrophilic substitution pathway.