Photoredox Nucleophilic (Radio)fluorination of Alkoxyamines
Herein, we report a photoredox nucleophilic (radio)fluorination using TEMPO-derived alkoxyamines, a class of substrates accessible in a single step from a diversity of readily available carboxylic acids, halides, alkenes, alcohols, aldehydes, boron reagents, and C–H bonds. This mild and versatile o...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
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American Chemical Society
2024
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| _version_ | 1811140072001503232 |
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| author | Ortalli, S Ford, J Trabanco, AA Tredwell, M Gouverneur, V |
| author_facet | Ortalli, S Ford, J Trabanco, AA Tredwell, M Gouverneur, V |
| author_sort | Ortalli, S |
| collection | OXFORD |
| description | Herein, we report a photoredox nucleophilic (radio)fluorination using TEMPO-derived alkoxyamines, a class of substrates accessible in a single step from a diversity of readily available carboxylic acids, halides, alkenes, alcohols, aldehydes, boron reagents, and C–H bonds. This mild and versatile one-electron pathway affords radiolabeled aliphatic fluorides that are typically inaccessible applying conventional nucleophilic substitution technologies due to insufficient reactivity and competitive elimination. Automation of this photoredox process is also demonstrated with a user-friendly and commercially available photoredox flow reactor and radiosynthetic platform, therefore expediting access to labeled aliphatic fluorides in high molar activity (A m ) for (pre)clinical evaluation. |
| first_indexed | 2024-09-25T04:16:10Z |
| format | Journal article |
| id | oxford-uuid:dc79eaef-69af-4d8d-8199-3b4b946a8077 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-09-25T04:16:10Z |
| publishDate | 2024 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:dc79eaef-69af-4d8d-8199-3b4b946a80772024-07-20T14:41:14ZPhotoredox Nucleophilic (Radio)fluorination of AlkoxyaminesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:dc79eaef-69af-4d8d-8199-3b4b946a8077EnglishJisc Publications RouterAmerican Chemical Society2024Ortalli, SFord, JTrabanco, AATredwell, MGouverneur, VHerein, we report a photoredox nucleophilic (radio)fluorination using TEMPO-derived alkoxyamines, a class of substrates accessible in a single step from a diversity of readily available carboxylic acids, halides, alkenes, alcohols, aldehydes, boron reagents, and C–H bonds. This mild and versatile one-electron pathway affords radiolabeled aliphatic fluorides that are typically inaccessible applying conventional nucleophilic substitution technologies due to insufficient reactivity and competitive elimination. Automation of this photoredox process is also demonstrated with a user-friendly and commercially available photoredox flow reactor and radiosynthetic platform, therefore expediting access to labeled aliphatic fluorides in high molar activity (A m ) for (pre)clinical evaluation. |
| spellingShingle | Ortalli, S Ford, J Trabanco, AA Tredwell, M Gouverneur, V Photoredox Nucleophilic (Radio)fluorination of Alkoxyamines |
| title | Photoredox Nucleophilic (Radio)fluorination of Alkoxyamines |
| title_full | Photoredox Nucleophilic (Radio)fluorination of Alkoxyamines |
| title_fullStr | Photoredox Nucleophilic (Radio)fluorination of Alkoxyamines |
| title_full_unstemmed | Photoredox Nucleophilic (Radio)fluorination of Alkoxyamines |
| title_short | Photoredox Nucleophilic (Radio)fluorination of Alkoxyamines |
| title_sort | photoredox nucleophilic radio fluorination of alkoxyamines |
| work_keys_str_mv | AT ortallis photoredoxnucleophilicradiofluorinationofalkoxyamines AT fordj photoredoxnucleophilicradiofluorinationofalkoxyamines AT trabancoaa photoredoxnucleophilicradiofluorinationofalkoxyamines AT tredwellm photoredoxnucleophilicradiofluorinationofalkoxyamines AT gouverneurv photoredoxnucleophilicradiofluorinationofalkoxyamines |