A general copper-mediated nucleophilic 18F 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 (SNAr) with [(18)F]F(-). In the ideal case, the (18)F fluorination of these substrates would be performed...
| Main Authors: | , , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2014
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| _version_ | 1826279601535451136 |
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| author | Tredwell, M Preshlock, S Taylor, N Gruber, S Huiban, M Passchier, J Mercier, J Génicot, C Gouverneur, V |
| author_facet | Tredwell, M Preshlock, S Taylor, N Gruber, S Huiban, M Passchier, J Mercier, J Génicot, C Gouverneur, V |
| author_sort | Tredwell, M |
| collection | OXFORD |
| 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 (SNAr) 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/K222 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. |
| first_indexed | 2024-03-07T00:01:11Z |
| format | Journal article |
| id | oxford-uuid:76028d73-e33f-4fef-9cb4-62f3ca0043d3 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T00:01:11Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | oxford-uuid:76028d73-e33f-4fef-9cb4-62f3ca0043d32022-03-26T20:12:55ZA general copper-mediated nucleophilic 18F fluorination of arenes.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:76028d73-e33f-4fef-9cb4-62f3ca0043d3EnglishSymplectic Elements at Oxford2014Tredwell, MPreshlock, STaylor, NGruber, SHuiban, MPasschier, JMercier, JGénicot, CGouverneur, VMolecules 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 (SNAr) 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/K222 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. |
| spellingShingle | Tredwell, M Preshlock, S Taylor, N Gruber, S Huiban, M Passchier, J Mercier, J Génicot, C Gouverneur, V A general copper-mediated nucleophilic 18F fluorination of arenes. |
| title | A general copper-mediated nucleophilic 18F fluorination of arenes. |
| title_full | A general copper-mediated nucleophilic 18F fluorination of arenes. |
| title_fullStr | A general copper-mediated nucleophilic 18F fluorination of arenes. |
| title_full_unstemmed | A general copper-mediated nucleophilic 18F fluorination of arenes. |
| title_short | A general copper-mediated nucleophilic 18F fluorination of arenes. |
| title_sort | general copper mediated nucleophilic 18f fluorination of arenes |
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