51571-29-0Relevant 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.
Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone
Soldatova, Natalia,Postnikov, Pavel,Kukurina, Olga,Zhdankin, Viktor V.,Yoshimura, Akira,Wirth, Thomas,Yusubov, Mekhman S.
, p. 18 - 20 (2017/02/10)
A straightforward synthesis of diaryliodonium salts is achieved by using Oxone as the stoichiometric oxidant. Slow addition is the key to obtaining good yields and purities of the reaction products, which are highly useful reagents in many different areas of organic synthesis.
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).
