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A General Copper‐Mediated Nucleophilic 18 F Fluorination of Arenes
Molecules labeled with fluorine‐18 are used as radiotracers for positron emission tomography. An important challenge is the labeling of arenes not amenable to aromatic nucleophilic substitution (S N Ar) with [ 18 F]F − . In the ideal case, the 18 F fluorination of these substrates would be performed...
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| Published in: | Angewandte Chemie International Edition 2014-07, Vol.53 (30), p.7751-7755 |
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| Main Authors: | , , , , , , , , |
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| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c846-b164b51dcb84b4f8188961b90b88303ea40fccb2d5573c6c937447a1aba4a58e3 |
| container_end_page | 7755 |
| container_issue | 30 |
| container_start_page | 7751 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 53 |
| creator | Tredwell, Matthew Preshlock, Sean M. Taylor, Nicholas J. Gruber, Stefan Huiban, Mickael Passchier, Jan Mercier, Joël Génicot, Christophe Gouverneur, Véronique |
| description | Molecules labeled with fluorine‐18 are used as radiotracers for positron emission tomography. An important challenge is the labeling of arenes not amenable to aromatic nucleophilic substitution (S
N
Ar) with [
18
F]F
−
. In the ideal case, the
18
F fluorination of these substrates would be performed through reaction of [
18
F]KF with shelf‐stable readily available precursors using a broadly applicable method suitable for automation. Herein, we describe the realization of these requirements with the production of
18
F arenes from pinacol‐derived aryl boronic esters (arylBPin) upon treatment with [
18
F]KF/K
222
and [Cu(OTf)
2
(py)
4
] (OTf=trifluoromethanesulfonate, py=pyridine). This method tolerates electron‐poor and electron‐rich arenes and various functional groups, and allows access to 6‐[
18
F]fluoro‐
L
‐DOPA, 6‐[
18
F]fluoro‐
m
‐tyrosine, and the translocator protein (TSPO) PET ligand [
18
F]DAA1106. |
| doi_str_mv | 10.1002/anie.201404436 |
| format | article |
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N
Ar) with [
18
F]F
−
. In the ideal case, the
18
F fluorination of these substrates would be performed through reaction of [
18
F]KF with shelf‐stable readily available precursors using a broadly applicable method suitable for automation. Herein, we describe the realization of these requirements with the production of
18
F arenes from pinacol‐derived aryl boronic esters (arylBPin) upon treatment with [
18
F]KF/K
222
and [Cu(OTf)
2
(py)
4
] (OTf=trifluoromethanesulfonate, py=pyridine). This method tolerates electron‐poor and electron‐rich arenes and various functional groups, and allows access to 6‐[
18
F]fluoro‐
L
‐DOPA, 6‐[
18
F]fluoro‐
m
‐tyrosine, and the translocator protein (TSPO) PET ligand [
18
F]DAA1106.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201404436</identifier><language>eng</language><ispartof>Angewandte Chemie International Edition, 2014-07, Vol.53 (30), p.7751-7755</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c846-b164b51dcb84b4f8188961b90b88303ea40fccb2d5573c6c937447a1aba4a58e3</citedby><cites>FETCH-LOGICAL-c846-b164b51dcb84b4f8188961b90b88303ea40fccb2d5573c6c937447a1aba4a58e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Tredwell, Matthew</creatorcontrib><creatorcontrib>Preshlock, Sean M.</creatorcontrib><creatorcontrib>Taylor, Nicholas J.</creatorcontrib><creatorcontrib>Gruber, Stefan</creatorcontrib><creatorcontrib>Huiban, Mickael</creatorcontrib><creatorcontrib>Passchier, Jan</creatorcontrib><creatorcontrib>Mercier, Joël</creatorcontrib><creatorcontrib>Génicot, Christophe</creatorcontrib><creatorcontrib>Gouverneur, Véronique</creatorcontrib><title>A General Copper‐Mediated Nucleophilic 18 F Fluorination of Arenes</title><title>Angewandte Chemie International Edition</title><description>Molecules labeled with fluorine‐18 are used as radiotracers for positron emission tomography. An important challenge is the labeling of arenes not amenable to aromatic nucleophilic substitution (S
N
Ar) with [
18
F]F
−
. In the ideal case, the
18
F fluorination of these substrates would be performed through reaction of [
18
F]KF with shelf‐stable readily available precursors using a broadly applicable method suitable for automation. Herein, we describe the realization of these requirements with the production of
18
F arenes from pinacol‐derived aryl boronic esters (arylBPin) upon treatment with [
18
F]KF/K
222
and [Cu(OTf)
2
(py)
4
] (OTf=trifluoromethanesulfonate, py=pyridine). This method tolerates electron‐poor and electron‐rich arenes and various functional groups, and allows access to 6‐[
18
F]fluoro‐
L
‐DOPA, 6‐[
18
F]fluoro‐
m
‐tyrosine, and the translocator protein (TSPO) PET ligand [
18
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N
Ar) with [
18
F]F
−
. In the ideal case, the
18
F fluorination of these substrates would be performed through reaction of [
18
F]KF with shelf‐stable readily available precursors using a broadly applicable method suitable for automation. Herein, we describe the realization of these requirements with the production of
18
F arenes from pinacol‐derived aryl boronic esters (arylBPin) upon treatment with [
18
F]KF/K
222
and [Cu(OTf)
2
(py)
4
] (OTf=trifluoromethanesulfonate, py=pyridine). This method tolerates electron‐poor and electron‐rich arenes and various functional groups, and allows access to 6‐[
18
F]fluoro‐
L
‐DOPA, 6‐[
18
F]fluoro‐
m
‐tyrosine, and the translocator protein (TSPO) PET ligand [
18
F]DAA1106.</abstract><doi>10.1002/anie.201404436</doi><tpages>5</tpages></addata></record> |
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| ispartof | Angewandte Chemie International Edition, 2014-07, Vol.53 (30), p.7751-7755 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_anie_201404436 |
| source | Wiley-Blackwell Read & Publish Collection |
| title | A General Copper‐Mediated Nucleophilic 18 F Fluorination of Arenes |
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