Synthesis and 18F Labeling of Alkenyl Sulfonyl Fluorides via an Unconventional Elimination Pathway
A successful Cu-catalyzed addition of both Cl and SO2OCF2H groups into alkenes allows us to discover the unusual reactivity of the SO2OCF2H group. As opposed to common sulfonic esters (RSO2-O-R'), in which the R' group is highly electrophilic, the SO2 moiety demonstrates higher electrophilicity in RSO2-OCF2H. The unexpected reactivity is further developed not only as a synthetic tool for well-functionalized alkenyl sulfonyl fluorides but also for the first 18F labeling of alkenyl sulfonyl fluorides.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:24 |
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| Enthalten in: |
Organic letters - 24(2022), 27 vom: 15. Juli, Seite 4992-4997 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zhang, Wei [VerfasserIn] |
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| Links: |
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| Themen: |
64B59K7U6Q |
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| Anmerkungen: |
Date Completed 18.07.2022 Date Revised 19.07.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/acs.orglett.2c02091 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM342928090 |
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| 245 | 1 | 0 | |a Synthesis and 18F Labeling of Alkenyl Sulfonyl Fluorides via an Unconventional Elimination Pathway |
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| 500 | |a Date Revised 19.07.2022 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a A successful Cu-catalyzed addition of both Cl and SO2OCF2H groups into alkenes allows us to discover the unusual reactivity of the SO2OCF2H group. As opposed to common sulfonic esters (RSO2-O-R'), in which the R' group is highly electrophilic, the SO2 moiety demonstrates higher electrophilicity in RSO2-OCF2H. The unexpected reactivity is further developed not only as a synthetic tool for well-functionalized alkenyl sulfonyl fluorides but also for the first 18F labeling of alkenyl sulfonyl fluorides | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a Alkenes |2 NLM | |
| 650 | 7 | |a Esters |2 NLM | |
| 650 | 7 | |a Sulfinic Acids |2 NLM | |
| 650 | 7 | |a sulfuryl fluoride |2 NLM | |
| 650 | 7 | |a 64B59K7U6Q |2 NLM | |
| 650 | 7 | |a Fluorides |2 NLM | |
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| 700 | 1 | |a Deng, Xiaoyun |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Feng-Xu |e verfasserin |4 aut | |
| 700 | 1 | |a Lin, Jin-Hong |e verfasserin |4 aut | |
| 700 | 1 | |a Xiao, Ji-Chang |e verfasserin |4 aut | |
| 700 | 1 | |a Liang, Steven H |e verfasserin |4 aut | |
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