Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones

Maruthi Kumar Narayanam; Gaoyuan Ma; Pier Alexandre Champagne; Kendall N. Houk; Jennifer M. Murphy

doi:10.1002/anie.201707274

Synthesis of [¹⁸F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones

Maruthi Kumar Narayanam
, Gaoyuan Ma
, Pier Alexandre Champagne
, Kendall N. Houk
, Jennifer M. Murphy

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

46 Scopus citations

Abstract

A practical method for radiofluorination of anilines with [¹⁸F]fluoride via N-arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective ¹⁸F-labeling to prepare [¹⁸F]fluoroarenes. The value of this methodology is further highlighted by successful application to prepare an ¹⁸F-labeled neuropeptide.

Original language	English (US)
Pages (from-to)	13006-13010
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	42
DOIs	https://doi.org/10.1002/anie.201707274
State	Published - Oct 9 2017
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

Keywords

click chemistry
fluorine-18
fluoroarene
peptide radiolabeling
sydnone

Access to Document

10.1002/anie.201707274

Cite this

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title = "Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones",

abstract = "A practical method for radiofluorination of anilines with [18F]fluoride via N-arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective 18F-labeling to prepare [18F]fluoroarenes. The value of this methodology is further highlighted by successful application to prepare an 18F-labeled neuropeptide.",

keywords = "click chemistry, fluorine-18, fluoroarene, peptide radiolabeling, sydnone",

author = "Narayanam, \{Maruthi Kumar\} and Gaoyuan Ma and Champagne, \{Pier Alexandre\} and Houk, \{Kendall N.\} and Murphy, \{Jennifer M.\}",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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AU - Houk, Kendall N.

AU - Murphy, Jennifer M.

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KW - click chemistry

KW - fluorine-18

KW - fluoroarene

KW - peptide radiolabeling

KW - sydnone

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