73178-07-1Relevant academic research and scientific papers
Facile synthesis of Koser's reagent and derivatives from iodine or aryl iodides
Merritt, Eleanor A.,Carneiro, Vania M. T.,Silva Jr., Luiz F.,Olofsson, Berit
, p. 7416 - 7419 (2010)
The first one-pot synthesis of neutral and electron-rich [hydroxy(tosyloxy)iodo]arenes (HTIBs) from iodine and arenes is presented, thereby avoiding the need for expensive iodine(III) precursors. A large set of HTIBs, including a polyfluorinated analogue, can be obtained from the corresponding aryl iodide under the same conditions. The reaction proceeds under mild conditions, without excess reagents, and is fast and high-yielding. Together, the two presented routes give access to a wide range of HTIBs, which are useful reagents in a variety of synthetic transformations.
Approach to the synthesis of indoline derivatives from diaryliodonium salts
Landge, Kamalkishor P.,Jang, Keun Sam,Lee, Sang Yeul,Chi, Dae Yoon
experimental part, p. 5705 - 5713 (2012/09/07)
An effective method of constructing the indoline moiety via intramolecular nucleophilic ring closure of a diaryliodonium salt is described. Diacetoxyiodoarene compounds (1a-1e) were converted into intermediate Koser's reagent and coupled with arylstannanes (7-10) to form diaryliodonium salts (11a-14e). Indoline compounds with different N-protecting groups, 15, 16, 17, and 18, were synthesized in higher yields by treating salts (11a-14e) with Cs2CO3 and TEMPO. Regardless of the electronic environment of five para-substituted iodoarenes and the natures of four N-protected arylstannane groups, the conversion proceeded well to afford corresponding indolines in yields of 72-84 and 70-84%, respectively.
Rapid microwave-promoted solvent-free synthesis of hypervalent iodine reagents
Zhou, Zhongshi,He, Xuehan
experimental part, p. 30 - 31 (2009/10/15)
Hypervalent hydroxy(sulfonyloxy)iodoarenes, hydroxy(phosphoryloxy) iodoarenes and bis(trifluoroactoxy)iodobenzene have been synthesised by a fast and convenient solvent-free ligand exchange reaction from the (diacetoxyiodo)arene under microwave irradiation, providing a simple method for the synthesis of these hypervalent iodine reagents in good yield and in a short time.
Facile one-pot preparation of [hydroxy(sulfonyloxy)iodo]arenes from iodoarenes with MCPBA in the presence of sulfonic acids
Yamamoto, Yukiharu,Togo, Hideo
, p. 2486 - 2488 (2007/10/03)
Various [hydroxy(sulfonyloxy)iodo]arenes were simply and efficiently obtained in high yields from the reaction of iodoarenes and MCPBA in the presence of sulfonic acids in a small amount of chloroform at room temperature, through a one-pot procedure. Georg Thieme Verlag Stuttgart.
Structure of and Electronic Interactions in Aromatic Polyvalent Iodine Compounds: a 13C NMR Study
Katritzky, Alan R.,Gallos, John K.,Durst, H. Dupont
, p. 815 - 822 (2007/10/02)
Available data on the structures, electronic substituent effects and 13C NMR spectra of aromatic polyvalent iodine compounds, particularly iodoso and iodoxy derivatives, are summarized and discussed.A series of aromatic tri- and penta-valent iodine compou
Regiospecific Synthesis of Aryl(2-furyl)iodonium Tosylates, a New Class of Iodonium Salts, from arenes and 2-(Trimethylsilyl)furans in Organic Solvents
Carman, Carol S.,Koser, Gerald F.
, p. 2534 - 2539 (2007/10/02)
The treatment of 2,5-bis(trimethylsilyl)furan with various arenes (ArI(OH)OTs) in acetonitrile/ methanol has been found to give aryliodonium tosylates in yields ranging from 62percent to 80percent.With 2-methyl-5-(trimethylsilyl)furan as the substrate, aryl(5-methyl-2-furyl)iodonium tosylates are likewise obtained in yields ranging from 61percent to 74percent.The reactions of arenes with 2-(trimethylsilyl)furan in methanol give aryl(2-furyl)iodonium tosylates in much lower yield (9-23percent) and are accompanied by the reductive decomposition of the hypervalent organoiodine component.To our knowledge, these are the first reported examples of aryl(furyl)iodonium salts.
Composition and a process for the preparation of [hydroxy(organosulfonyloxy)iodo]arenes and their use in a regiospecific synthesis of diaryliodonium salts
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, (2008/06/13)
[Hydroxy(organosulfonyloxy)iodo]arenes are synthesized in neutral organic solvents by the reaction of ring-substituted [hydroxy(organosulfonyloxy)iodo]benzenes with iodoarenes via ligand transfer. The produced compounds are reacted with (triorganosilyl) arenes or (trihalosilyl)arenes in neutral organic solvents to produce diaryliodonium salts. The diaryliodonium salt synthesis proceeds in regiospecific fashion, aryliodination occurring at the point of attachment of the silicon atom in the silylarenes.
benzene, a Versatile Reagent for the Mild Oxidation of Aryl Iodides at the Iodine Atom by Ligand Transfer
Koser, Gerald F.,Wettach, Richard H.
, p. 1542 - 1543 (2007/10/02)
Treatment of a variety of aryl iodides with benzene (1) under mild conditions resulted in ligand transfer, and new arenes were obtained.However, with some substrates containing proximate functional groups cyclic iodonium salts and iodinanes resulted.The reaction between 1 and 2-iodothiophene took a distinctly different course.
