jo9b03193_si_001.pdf (2.79 MB)
Fluoromethoxymethylation of Nitrogen Heterocyclic Compounds with Fluoromethyl Iodide
journal contribution
posted on 2020-01-13, 22:29 authored by Rongkang Wang, Tianqi Ding, Lvqi Jiang, Wujuan He, Wenbin YiThe
fluoromethoxymethylation of nitrogen heterocyclic compounds
with fluoromethyl iodide has been reported for the first time. In
this reaction, a number of unexplored fluoromethoxymethylated nitrogen
heterocyclic compounds including indoles, carbazoles, and 1H-indazoles were efficiently formed. Mechanistic studies
indicated that this transformation consists of electrophilic monofluoromethylation,
rapid hydrolysis, and another electrophilic monofluoromethylation.
This method makes it possible to synthesize complex bioactive molecules
containing a CH2OCH2F group, which have the
potential to be a new series of fluorine-containing chemical entities
for medicinal chemists.
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electrophilic monofluoromethylationseriesnitrogen heterocyclic compoundsFluoromethoxymethylationIodideindolecarbazolefluorine-containing chemical entitiesMechanisticfluoromethoxymethylationiodidetransformationchemistmoleculeFluoromethylmethodentitybioactiveNitrogen Heterocyclic CompoundsindazolehydrolysisCH 2 OCH 2 F groupfluoromethoxymethylated nitrogen heterocyclic compounds
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