Copper-catalyzed [18F]fluorination of (Mesityl)(aryl)iodonium salts

Naoko Ichiishi; Allen F. Brooks; Joseph J. Topczewski; Melissa E. Rodnick; Melanie S. Sanford; Peter J.H. Scott

doi:10.1021/ol501243g

Copper-catalyzed [¹⁸F]fluorination of (Mesityl)(aryl)iodonium salts

Naoko Ichiishi, Allen F. Brooks, Joseph J. Topczewski, Melissa E. Rodnick, Melanie S. Sanford, Peter J.H. Scott

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

184 Scopus citations

Abstract

A practical, rapid, and highly regioselective Cu-catalyzed radiofluorination of (mesityl)(aryl)iodonium salts is described. This protocol utilizes [¹⁸F]KF to access ¹⁸F-labeled electron-rich, -neutral, and -deficient aryl fluorides under a single set of mild conditions. This methodology is applied to the synthesis of protected versions of two important radiotracers: 4-[¹⁸F]fluorophenylalanine and 6-[ ¹⁸F]fluoroDOPA.

Original language	English (US)
Pages (from-to)	3224-3227
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	12
DOIs	https://doi.org/10.1021/ol501243g
State	Published - Jun 20 2014

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title = "Copper-catalyzed [18F]fluorination of (Mesityl)(aryl)iodonium salts",

abstract = "A practical, rapid, and highly regioselective Cu-catalyzed radiofluorination of (mesityl)(aryl)iodonium salts is described. This protocol utilizes [18F]KF to access 18F-labeled electron-rich, -neutral, and -deficient aryl fluorides under a single set of mild conditions. This methodology is applied to the synthesis of protected versions of two important radiotracers: 4-[18F]fluorophenylalanine and 6-[ 18F]fluoroDOPA.",

author = "Naoko Ichiishi and Brooks, {Allen F.} and Topczewski, {Joseph J.} and Rodnick, {Melissa E.} and Sanford, {Melanie S.} and Scott, {Peter J.H.}",

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doi = "10.1021/ol501243g",

language = "English (US)",

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T1 - Copper-catalyzed [18F]fluorination of (Mesityl)(aryl)iodonium salts

AU - Ichiishi, Naoko

AU - Brooks, Allen F.

AU - Topczewski, Joseph J.

AU - Rodnick, Melissa E.

AU - Sanford, Melanie S.

AU - Scott, Peter J.H.

PY - 2014/6/20

Y1 - 2014/6/20

N2 - A practical, rapid, and highly regioselective Cu-catalyzed radiofluorination of (mesityl)(aryl)iodonium salts is described. This protocol utilizes [18F]KF to access 18F-labeled electron-rich, -neutral, and -deficient aryl fluorides under a single set of mild conditions. This methodology is applied to the synthesis of protected versions of two important radiotracers: 4-[18F]fluorophenylalanine and 6-[ 18F]fluoroDOPA.

AB - A practical, rapid, and highly regioselective Cu-catalyzed radiofluorination of (mesityl)(aryl)iodonium salts is described. This protocol utilizes [18F]KF to access 18F-labeled electron-rich, -neutral, and -deficient aryl fluorides under a single set of mild conditions. This methodology is applied to the synthesis of protected versions of two important radiotracers: 4-[18F]fluorophenylalanine and 6-[ 18F]fluoroDOPA.

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Copper-catalyzed [¹⁸F]fluorination of (Mesityl)(aryl)iodonium salts

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