73177-97-6Relevant 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
experimental part, p. 7416 - 7419 (2011/02/22)
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.
Fast and high-yield microreactor syntheses of ortho -substituted [ 18F]Fluoroarenes from reactions of [18F]Fluoride ion with diaryliodonium salts
Chun, Joong-Hyun,Lu, Shuiyu,Lee, Yong-Sok,Pike, Victor W.
supporting information; experimental part, p. 3332 - 3338 (2010/08/20)
A microreactor was applied to produce ortho-substituted [ 18F]fluoroarenes from the reactions of cyclotron-produced [ 18F]fluoride ion (t1/2 = 109.7 min) with diaryliodonium salts. The microreactor provided a very convenient means for running sequential reactions rapidly with small amounts of reagents under well-controlled conditions, thereby allowing reaction kinetics to be followed and Arrhenius activation energies (Ea) to be measured. Prepared symmetrical iodonium chlorides (Ar2I+Cl-) rapidly (6H4, 51%) to high (Ar = Ph or 2-MeC6H4, 85%) decay-corrected radiochemical yields (RCYs) of a single radioactive product (Ar18F). Reaction velocity with respect to Ar group was 2-MeOC6H4 6H4. Activation energies were in the range 18-28 kcal/mol. Prepared unsymmetrical salts (e.g., 2-RC6H 4I+2′-R′C6H4X -; X = Cl or OTs) also rapidly gave two products (2-RC 6H418F and 2-R′C6H 418F) in generally high total RCYs (79-93%). Selectivity for product [18F]fluoroarene was controlled by the nature of the ortho substituents. The power of ortho substituents to impart an ortho-effect was in the following order:, 2,6-di-Me > 2,4,6-tri-Me > Br > Me > Et ≈ iPr ? H > OMe. For (2-methyphenyl)(phenyl)iodonium chloride, the time-course of reaction product selectivity was constant and consistent with the operation of the Curtin-Hammett principle. These results will aid in the design of diaryliodonium salt precursors to 18F- labeled tracers for molecular imaging. This article not subject to U.S. Copyright. Published 2010 by the American Chemical Society.
Conformational structure and energetics of 2- methylphenyl(2′methoxyphenyl)iodonium chloride: Evidence for solution clusters
Lee, Yong-Sok,Hodoscek, Milan,Chun, Joong-Hyun,Pike, Victor W.
supporting information; experimental part, p. 10418 - 10423 (2010/11/05)
Diaryliodonium salts allow the efficient incorporation of cyclotronproduced [18F]fluoride ions into electron-rich and electron-deficient arenes to provide potential radiotracers for molecular imaging in vivo with positron emission tomography (P
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.
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.
