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Direct C–H Alpha Arylation of Enones with ArI(O2CR)2 Reagents

submitted on 20.10.2019, 20:05 and posted on 23.10.2019, 15:52 by 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.


NIH R01 GM123098

NSF CAREER 1752244


Email Address of Submitting Author


Temple University


United States

ORCID For Submitting Author


Declaration of Conflict of Interest

The authors declare no competing financial interests