73177-92-1Relevant academic research and scientific papers
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.
Facile synthesis of substituted diaryliodonium tosylates by treatment of aryltributylstannanes with Koser's reagent
Pike, Victor W.,Butt, Faisal,Shah, Aneela,Widdowson, David A.
, p. 245 - 248 (2007/10/03)
A facile synthesis of substituted diaryliodonium tosylates (toluene-p-sulfonates) was developed, based on the treatment of substituted aryltributylstannanes with Koser's reagent [hydroxy(tosyloxy)iodobenzene]. In this manner, several new diaryliodonium sa
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.
New Methodology in Iodonium Salt Synthesis. Reactions of arenes with Aryltrimethylsilanes
Koser, Gerald F.,Wettach, Richard H.,Smith, Carol S.
, p. 1543 - 1544 (2007/10/02)
arenes react with aryltrimethylsilanes in acetonitrile to give diaryliodonium tosylates.The phenyliodinations proceed with silicon-carbon bond cleavage, thus allowing control of substituent placement in both rings.With bis(trimethyl
