Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 33, Pages 9930-9934Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201704175
Keywords
electrophilic substitution; fluorine; monofluoromethylation; sulfonium ylides; synthetic methods
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Funding
- National Natural Science Foundation of China [21625206, 21632009, 21372247, 21572258, 21572259, 21421002]
- Chinese Academy of Sciences [XDB20000000]
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Two electrophilic monofluoromethylating reagents, monofluoromethyl(phenyl) sulfonium bis(carbomethoxy)methylide (3a) and monofluoromethyl(4-nitrophenyl)sulfonium bis(carbomethoxy)methylide (3b), 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.
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