- An Investigation of (Diacetoxyiodo)arenes as Precursors for Preparing No-Carrier-Added [18F]Fluoroarenes from Cyclotron-Produced [18F]Fluoride Ion
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Treatment of (diacetoxyiodo)arenes (1a-1u) with cyclotron-produced [18F]fluoride ion rapidly affords no-carrier-added [18F]fluoroarenes (2a-2u) in useful yields and constitutes a new method for converting substituted iodoarenes into substituted [18F]fluoroarenes in just two steps.
- Haskali, Mohammad B.,Telu, Sanjay,Lee, Yong-Sok,Morse, Cheryl L.,Lu, Shuiyu,Pike, Victor W.
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p. 297 - 302
(2016/01/15)
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- A mild carbon-boron bond formation from diaryliodonium salts
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The direct metal-free borylation of diaryliodonium salts with diboron reagents is now demonstrated to be a feasible process toward formation of aryl boronic esters without any additive or catalysts, and it can be extended to a two-step C-C coupling of both aryl groups of the initial diaryliodonium reagent.
- Miralles,Romero,Fernández,Mu?iz
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supporting information
p. 14068 - 14071
(2015/09/15)
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- Fast and high-yield microreactor syntheses of ortho -substituted [ 18F]Fluoroarenes from reactions of [18F]Fluoride ion with diaryliodonium salts
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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.
- Chun, Joong-Hyun,Lu, Shuiyu,Lee, Yong-Sok,Pike, Victor W.
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supporting information; experimental part
p. 3332 - 3338
(2010/08/20)
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- Synthesis of 3-aryloxy-2-iodoemodines by oxidation of emodin with (diacetoxyiodo)arenes
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Hypervalent iodine oxidation of emodin (1) with various (diacetoxyiodo)arenes 2a-f in potassium hydroxide/methanol leading to 3-aryloxy-1,8-dihydroxy-2-iodo-anthraquinones 4a-f is reported. Mechanistic studies showed reaction via iodonium ylides. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Daub, Katja S.,Habermann, Bernd,Hahn, Thilo,Teich, Lars,Eger, Kurt
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p. 894 - 898
(2007/10/03)
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- FURTHER FUNCTIONAL GROUP OXIDATIONS USING SODIUM PERBORATE
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Sodium perborate in acetic acid is an effective reagent for the oxidation of aromatic aldehydes to carboxylic acids, iodoarenes to (diacetoxyiodo)arenes, azines to N-oxides, and various types of sulfur heterocycles to S,S-dioxides.Nitriles are unaffected by the reagent in acetic acid, but undergo smooth hydration to amides when aqueous methanol is employed as solvent.
- McKillop, Alexander,Kemp, Duncan
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p. 3299 - 3306
(2007/10/02)
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