64846-46-4Relevant academic research and scientific papers
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.
Development of Imino-λ3-iodanes with Improved Reactivity for Metal-Free [2+2+1] Cycloaddition-Type Reactions
Baba, Takafumi,Takahashi, Shunsuke,Kambara, Yui,Yoshimura, Akira,Nemykin, Victor N.,Zhdankin, Viktor V.,Saito, Akio
supporting information, p. 3860 - 3864 (2017/10/09)
Aiming at the enhancement of electrophilicity of imino-λ3-iodanes, we have developed (tosylimino)pentafluorophenyl-λ3-iodane, which shows superior reactivity compared to the commonly used (tosylimino)phenyl-λ3-iodane in the [2+2+1]-type synthesis of imidazoles. (Figure presented.).
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.
Direct and convenient synthesis of [bis(trifluoroacetoxy)iodo]arenes from iodoarenes
Hossain, Delwar,Kitamura, Tsugio
, p. 142 - 144 (2007/10/03)
An easy, safe, and effective method for preparing [bis-(trifluoroacetoxy) iodo]arenes, ArI(OCOCF3)2, in high yields from some iodoarenes are reported, using a K2S2O8/CF 3COOH/CH2Cl2 system. This procedure avoids the use of high temperature and severe reaction conditions.
