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

preprint
submitted on 20.10.2019 and posted on 23.10.2019 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.

Funding

NIH R01 GM123098

NSF CAREER 1752244

History

Email Address of Submitting Author

sarahw@temple.edu

Institution

Temple University

Country

United States

ORCID For Submitting Author

0000-0002-4797-0181

Declaration of Conflict of Interest

The authors declare no competing financial interests

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