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submitted on 20.10.2019 and posted on 23.10.2019by Felipe Cesar Sousa e Silva, Nguyen T Van, Sarah Wengryniuk
Herein, we report the
metal-free direct C–H arylation of enones mediated by hypervalent iodine
reagents. The reaction proceeds via a reductive iodonium Claisen rearrangement of
in situ b-pyridinium silyl enol ethers. The aryl groups are
derived from ArI(O2CCF3)2 reagents, which are
readily accessed from the parent iodoarenes. It is tolerant of a wide range of
substitution patterns and the incorporated arenes maintain the valuable iodine
functional handle. Mechanistic investigations implicate arylation via an
umpoled “enolonium” species and that the presence of a b-pyridinium moiety is critical for desired C–C bond formation.