16669-00-4Relevant articles and documents
SYNTHESIS OF HYPERVALENT IODINE REAGENTS WITH DIOXYGEN
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Paragraph 0105-0106, (2019/01/15)
Methods of synthesis of hypervalent iodine reagents and methods for oxidation of organic compounds are disclosed.
Oxidation Catalysis by an Aerobically Generated Dess–Martin Periodinane Analogue
Maity, Asim,Hyun, Sung-Min,Wortman, Alan K.,Powers, David C.
supporting information, p. 7205 - 7209 (2018/05/29)
Hypervalent iodine(V) reagents, such as Dess–Martin periodinane (DMP) and 2-iodoxybenzoic acid (IBX), are broadly useful oxidants in chemical synthesis. Development of strategies to generate these reagents from dioxygen (O2) would immediately enable use of O2 as a terminal oxidant in a broad array of substrate oxidation reactions. Recently we disclosed the aerobic synthesis of I(III) reagents by intercepting reactive oxidants generated during aldehyde autoxidation. In this work, aerobic oxidation of iodobenzenes is coupled with disproportionation of the initially generated I(III) compounds to generate I(V) reagents. The aerobically generated I(V) reagents exhibit substrate oxidation chemistry analogous to that of DMP. The developed aerobic generation of I(V) has enabled the first application of I(V) intermediates in aerobic oxidation catalysis.
Catalyst-Free Aromatic Radiofluorination via Oxidized Iodoarene Precursors
Kwon, Young-Do,Son, Jeongmin,Chun, Joong-Hyun
supporting information, p. 7902 - 7906 (2019/01/04)
Oxidized iodoarenes (OIAs), prepared via mCPBA-mediated oxidation, have been demonstrated as versatile precursors for the synthesis of [18F]fluoroarenes in the absence of catalysts. OIAs have been identified as intermediates in single-pot syntheses of iodonium salts and ylides but have never been recognized as radiofluorination precursors. Here, the isolated OIAs were used without any catalysts to produce functionalized [18F]fluoroarenes, regardless of the electronic nature of the arenes. This method was also applied to the production of radiolabeling synthons for use as aromatic 18F-labeled building blocks.
Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species
Yusubov, Mekhman S.,Nemykin, Victor N.,Zhdankin, Viktor V.
experimental part, p. 5745 - 5752 (2010/10/02)
Several transition metal-mediated oxidations using hypervalent iodine species are reported. A convenient procedure for preparation of iodylarenes via RuCl3-catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species, which are excellent oxidants toward alcohols and hydrocarbons in situ. A broad range of substrates can be oxidized to carbonyl compounds by a tandem catalytic system based on the Ru(III)-catalyzed reoxidation of ArIO to ArIO2 using Oxone as oxidant. It was shown that electrophilic iodine(III) species, originating from oligomeric iodosylbenzene sulfate (PhIO)3SO3, are efficient oxygenating agents in catalytic oxidation of aromatic hydrocarbons in the presence of metalloporphyrin complexes.
RuCl3-catalyzed oxidation of iodoarenes with peracetic acid: New facile preparation of iodylarenes
Koposov, Alexey Y.,Karimov, Rashad R.,Pronin, Andrey A.,Skrupskaya, Tatyana,Yusubov, Mekhman S.,Zhdankin, Viktor V.
, p. 9912 - 9914 (2007/10/03)
New facile methodology for the preparation of pentavalent iodine compounds using peracetic acid as an oxidant in the presence of catalytic amounts of ruthenium trichloride is described. The new procedure allows the preparation of several previously unknown iodylarenes bearing strongly electron-withdrawing CF3 groups in the aromatic ring.
Syntheses of (diacetoxyiodo)arenes or iodylarenes from iodoarenes, with sodium periodate as the oxidant
Kazmierczak, Pawel,Skulski, Lech,Kraszkiewicz, Lukasz
, p. 881 - 891 (2007/10/03)
Easy, safe, and effective novel methods for preparing either (diacetoxyiodo)-(arenes, ArI(OAc)2, or iodylarenes, ArIO2, from the corresponding iodoarenes, ArI, using sodium periodate as the oxidant are presented in this paper. In order to obtain 2- and 4-iodylbenzoic acids, the respective sodium salts of 2- and 4-iodobenzoic acids should be used as the starting substrates, because mixtures containing the corresponding iodosyl derivatives as the main products along with the intended iodyl compounds are produced from the free parent acids.
