64846-47-5Relevant 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.
An Investigation of (Diacetoxyiodo)arenes as Precursors for Preparing No-Carrier-Added [18F]Fluoroarenes from Cyclotron-Produced [18F]Fluoride Ion
Haskali, Mohammad B.,Telu, Sanjay,Lee, Yong-Sok,Morse, Cheryl L.,Lu, Shuiyu,Pike, Victor W.
, p. 297 - 302 (2016/01/15)
Treatment of (diacetoxyiodo)arenes (1a-1u) with cyclotron-produced [18F]fluoride ion rapidly affords no-carrier-added [18F]fluoroarenes (2a-2u) in useful yields and constitutes a new method for converting substituted iodoarenes into substituted [18F]fluoroarenes in just two steps.
A general and convenient preparation of [Bis(trifluoroacetoxy)iodo] perfluoroalkanes and [Bis(trifluoroacetoxy)iodo] arenes by oxidation of organic iodides using Oxone and trifluoroacetic acid
Zagulyaeva, Aleksandra A.,Yusubov, Mekhman S.,Zhdankin, Viktor V.
supporting information; experimental part, p. 2119 - 2122 (2010/06/12)
"Chemical Equation Presented" [Bis(trifiuoroacetoxy)iodo] perfiuoroalkanes CnF2n+1I(OC-OCF3)2 (n = 4, 6, 8, 10, 12) can be conveniently prepared by the oxidation of the corresponding perfluoroalkyl iodides with Oxone in trifluoroacetic acid at room temperature and subsequently converted to the stable [hydroxy(tosyloxy)-iodo] perfluoroalkanes, CnF2n+1I(OH)OTs, by treatment with p-toluenesulfonic acid. This general and convenient procedure has been further extended to the synthesis of various [bis(trifluoroacetoxy)iodo]arenes, ArI(OCOCF3)2.