87167-84-8Relevant articles and documents
Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents
Sousa E Silva, Felipe Cesar,Van, Nguyen T.,Wengryniuk, Sarah E.
supporting information, p. 64 - 69 (2020/01/22)
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 incorporated arenes maintain the valuable iodine functional handle. Mechanistic investigations implicate arylation via an umpoled "enolonium" species and show that the presence of a β-pyridinium moiety is critical for the desired C-C bond formation.
Easy preparation of [bis(trifluoroacetoxy)iodo]arenes from iodoarenes, with sodium percarbonate as the oxidant
Kazmierczak, Pawel,Skulski, Lech
, p. 810 - 812 (2007/10/03)
Easy and effective preparations of the nearly pure [bis(trifluoroacetoxy) iodo]arenes, ArI(OCOCF)3, from some iodoarenes, ArI, are reported, using an anhydrous) sodium (percarbonate/(CF3CO)2O/CH 2Cl2 system. The colorless, freshly prepared (ArI(OCOCF)3)2 thus obtained were 98-99% pure (by iodometry).