Nucleophilic 18F-Labeling of Spirocyclic Iodonium Ylide or Boronic Pinacol Ester Precursors - Advantages and Disadvantages

Ida Nymann Petersen; Jesper Langgaard Kristensen; Matthias Manfred Herth

doi:10.1002/ejoc.201601448

Nucleophilic ¹⁸F-Labeling of Spirocyclic Iodonium Ylide or Boronic Pinacol Ester Precursors - Advantages and Disadvantages

Ida Nymann Petersen, Jesper Langgaard Kristensen, Matthias Manfred Herth^*

^*Corresponding author for this work

17 Citations (Scopus)

Abstract

The field of labeling electron-rich aryl compounds with nucleophilic [¹⁸F]fluoride has recently expanded with radiofluorination strategies that apply boronic esters or spirocyclic iodonium ylides as precursors. Herein, we present a direct comparison of these strategies by using nine chemically diverse model compounds. In general, spirocyclic iodonium ylides outperform the boronic esters.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	3
Pages (from-to)	453-458
Number of pages	6
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.201601448
Publication status	Published - 18 Jan 2017

Keywords

Comparative studies
Isotopic labeling
Nucleophilic substitution
Spiro compounds
Ylides

Access to Document

10.1002/ejoc.201601448

Cite this

Nucleophilic ¹⁸F-Labeling of Spirocyclic Iodonium Ylide or Boronic Pinacol Ester Precursors - Advantages and Disadvantages. / Petersen, Ida Nymann; Kristensen, Jesper Langgaard ; Herth, Matthias Manfred.
In: European Journal of Organic Chemistry, Vol. 2017, No. 3, 18.01.2017, p. 453-458.

Research output: Contribution to journal › Journal article › Research › peer-review

@article{57f5f573ad304444b67f30e8487c6c42,

title = "Nucleophilic 18F-Labeling of Spirocyclic Iodonium Ylide or Boronic Pinacol Ester Precursors - Advantages and Disadvantages",

abstract = "The field of labeling electron-rich aryl compounds with nucleophilic [18F]fluoride has recently expanded with radiofluorination strategies that apply boronic esters or spirocyclic iodonium ylides as precursors. Herein, we present a direct comparison of these strategies by using nine chemically diverse model compounds. In general, spirocyclic iodonium ylides outperform the boronic esters.",

keywords = "Comparative studies, Isotopic labeling, Nucleophilic substitution, Spiro compounds, Ylides",

author = "Petersen, {Ida Nymann} and Kristensen, {Jesper Langgaard} and Herth, {Matthias Manfred}",

year = "2017",

month = jan,

day = "18",

doi = "10.1002/ejoc.201601448",

language = "English",

volume = "2017",

pages = "453--458",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",

number = "3",

}

TY - JOUR

T1 - Nucleophilic 18F-Labeling of Spirocyclic Iodonium Ylide or Boronic Pinacol Ester Precursors - Advantages and Disadvantages

AU - Petersen, Ida Nymann

AU - Kristensen, Jesper Langgaard

AU - Herth, Matthias Manfred

PY - 2017/1/18

Y1 - 2017/1/18

N2 - The field of labeling electron-rich aryl compounds with nucleophilic [18F]fluoride has recently expanded with radiofluorination strategies that apply boronic esters or spirocyclic iodonium ylides as precursors. Herein, we present a direct comparison of these strategies by using nine chemically diverse model compounds. In general, spirocyclic iodonium ylides outperform the boronic esters.

AB - The field of labeling electron-rich aryl compounds with nucleophilic [18F]fluoride has recently expanded with radiofluorination strategies that apply boronic esters or spirocyclic iodonium ylides as precursors. Herein, we present a direct comparison of these strategies by using nine chemically diverse model compounds. In general, spirocyclic iodonium ylides outperform the boronic esters.

KW - Comparative studies

KW - Isotopic labeling

KW - Nucleophilic substitution

KW - Spiro compounds

KW - Ylides

U2 - 10.1002/ejoc.201601448

DO - 10.1002/ejoc.201601448

M3 - Journal article

AN - SCOPUS:85010693212

SN - 1434-193X

VL - 2017

SP - 453

EP - 458

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 3

ER -

Nucleophilic 18F-Labeling of Spirocyclic Iodonium Ylide or Boronic Pinacol Ester Precursors - Advantages and Disadvantages

Abstract

Keywords

Access to Document

Fingerprint

Cite this

Nucleophilic ¹⁸F-Labeling of Spirocyclic Iodonium Ylide or Boronic Pinacol Ester Precursors - Advantages and Disadvantages