69180-49-0Relevant academic research and scientific papers
N -Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts to Generate α,β-Unsaturated Ketones
Rajkiewicz, Adam A.,Kalek, Marcin
supporting information, p. 1906 - 1909 (2018/04/16)
An organocatalyzed metal-free, direct olefination of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C-H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)aryl-vinyl ketones in good yields. The retention of the double bond configuration is uniformly observed, and the application of 2-methoxyphenyl auxiliary group in iodonium salts secures a complete selectivity of the vinyl transfer.
Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles
Zhao, Chun-Yang,Li, Kun,Pang, Yu,Li, Jia-Qing,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang
supporting information, p. 1919 - 1925 (2018/03/28)
A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).
Generation of Aryl Radicals through Reduction of Hypervalent Iodine(III) Compounds with TEMPONa: Radical Alkene Oxyarylation
Hartmann, Marcel,Li, Yi,Mück-Lichtenfeld, Christian,Studer, Armido
, p. 3485 - 3490 (2016/03/05)
A novel method for selective generation of aryl radicals from diaryliodonium salts and iodanylidene malonates with sodium 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPONa) as a single-electron transfer (SET) reducing reagent is described. In the presence of various alkenes, aryl radicals formed after SET-reduction of hypervalent iodine compounds undergo alkene addition and the adduct radicals that are thus generated are efficiently trapped by the concomitantly generated TEMPO radical to eventually afford oxyarylated products in moderate to very good yields. The efficiency of aryl radical generation of various iodine(III) reagents is studied and the generation of an iodanylidene malonate aryl radical is also investigated by computational methods.
A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts
Qin, Linlin,Hu, Bao,Neumann, Kiel D.,Linstad, Ethan J.,McCauley, Katelyenn,Veness, Jordan,Kempinger, Jayson J.,DiMagno, Stephen G.
supporting information, p. 5919 - 5924 (2015/09/22)
Diaryliodonium salts are powerful and widely used arylating agents in organic chemistry. Here we report a scalable synthesis of densely functionalized diaryliodonium salts from aryl iodides under mild conditions. This two-step, one-pot process has remarkable functional group tolerance, is compatible with commonly employed acid-labile protective group strategies, avoids heavy metal and transition metal reagents, and provides a direct route to stable precursors to PET imaging agents.
Synthesis of ionic-liquid-supported diaryliodonium salts
Kumar Muthyala, Manoj,Choudhary, Sunita,Pandey, Khima,Shelke, Ganesh M.,Jha, Mukund,Kumar, Anil
supporting information, p. 2365 - 2370 (2014/04/17)
The synthesis of ionic-liquid-supported diaryliodonium salts is described. The synthesis is simple and practical, and the ionic liquid products require no chromatographic purification. The ionic-liquid-supported diaryliodonium salts are quite stable, and they did not show any sign of decomposition or loss of reactivity, even after being stored for one month at 5 °C. The reactivity of these salts was explored in the phenylation of substituted phenols and carboxylic acids, and the corresponding diaryl ethers and aryl esters, respectively, were synthesized in good to excellent yields and with high purities.
Synthesis and reactivity of aryl(alkynyl)iodonium salts
Dixon, Luke I.,Carroll, Michael A.,Gregson, Thomas J.,Ellames, George J.,Harrington, Ross W.,Clegg, William
supporting information, p. 2334 - 2345 (2013/05/21)
The first practical, yet simple, preparation of aryl(alkynyl)iodonium trifluoroacetate salts is described. The generic nature of this synthetic method has allowed the production of a range of aryl(alkynyl)iodonium trifluoroacetate salts with independent variation of both the alkynyl and aryliodo groups in yields of 30-85 %. Application of these new reagents to the synthesis of a series of 2-arylfuro[3,2-c]pyridines (40-64 %) highlights the potential of this class of materials as precursors to bioactive heterocyclic structures. These experiments have also demonstrated that, in this case, the effect of the aryliodo group on the reaction is negligible.
Design, preparation, X-ray crystal structure, and reactivity of o-alkoxyphenyliodonium bis(methoxycarbonyl)methanide, a highly soluble carbene precursor
Zhu, Chenjie,Yoshimura, Akira,Ji, Lei,Wei, Yunyang,Nemykin, Victor N.,Zhdankin, Viktor V.
, p. 3170 - 3173 (2012/08/07)
The preparation, X-ray structure, and reactivity of new, highly soluble, and reactive iodonium ylides derived from malonate methyl ester and bearing an ortho substituent on the phenyl ring are reported. These new reagents show higher reactivity than common phenyliodonium ylides in the Rh-catalyzed cyclopropanation, C-H insertion, and transylidation reactions under homogeneous conditions.
New highly soluble dimedone-derived iodonium ylides: Preparation, X-ray structure, and reaction with carbodiimide leading to oxazole derivatives
Zhu, Chenjie,Yoshimura, Akira,Solntsev, Pavlo,Ji, Lei,Wei, Yunyang,Nemykin, Victor N.,Zhdankin, Viktor V.
, p. 10108 - 10110 (2012/11/13)
Highly soluble dimedone-derived o-alkoxyphenyliodonium ylides have been prepared and characterized by single crystal X-ray diffraction. These new iodonium ylides are useful reagents for the preparation of oxazole derivatives by reaction with carbodiimides. The Royal Society of Chemistry 2012.
Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts
Graskemper, Joseph W.,Wang, Bijia,Qin, Linlin,Neumann, Kiel D.,Dimagno, Stephen G.
supporting information; experimental part, p. 3158 - 3161 (2011/08/06)
For the first time it is shown that exceptionally electron-rich arene rings can be fluorinated exclusively during the reductive elimination reactions of diaryliodonium fluorides. The 5-methoxy[2.2]paracyclophan-4-yl directing group simultaneously reduces unproductive aryne chemistry and eliminates ligand exchange reactions by a combination of steric and electronic effects. Use of the cyclophane directing group permits an unprecedented degree of control in fluorination reactions of diaryliodonium salts.
O-alkoxyphenyliminoiodanes: Highly efficient reagents for the catalytic aziridination of alkenes and the metal-free amination of organic substrates
Yoshimura, Akira,Nemykin, Victor N.,Zhdankin, Viktor V.
supporting information; experimental part, p. 10538 - 10541 (2011/11/12)
Efficient nitrene precursors: Highly reactive iminoiodane-based nitrene precursors were prepared from ortho-alkoxyiodobenzenes. Owing to the presence of the ortho-substituent on the phenyl ring, these new iminoiodanes have excellent solubility in organic
