Direct C-H α-Arylation of Enones with ArI(O₂CR)₂ Reagents.

ABSTRACT: α-Arylation of α,β-unsaturated ketones constitutes a powerful synthetic transformation. It is most commonly achieved via cross-coupling of α-haloenones, but this stepwise strategy requires prefunctionalized substrates and expensive catalysts. Direct enone C-H α-arylation would offer an atom- and step-economical alternative, but such reports are scarce. 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-generated β-pyridinium silyl enol ethers. The aryl groups are derived from ArI(O₂CCF₃)₂ reagents, which are readily accessed from the parent iodoarenes. The reaction is tolerant of a wide range of substitution patterns, and the

SUBMITTER: Sousa E Silva FC 

PROVIDER: S-EPMC7067356 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature