Nucleophilic F-18-Labeling of Spirocyclic Iodonium Ylide or Boronic Pinacol Ester Precursors: Advantages and Disadvantages
The field of labeling electron-rich aryl compounds with nucleophilic [F-18] fluoride has recently expanded with radio-fluorination strategies that apply boronic esters or spirocyclic iodonium ylides as precursors. Herein, we present a direct comparison of these strategies by using nine chemically di...
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| Published in | European journal of organic chemistry Vol. 2017; no. 3; pp. 453 - 458 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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18.01.2017
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| Abstract | The field of labeling electron-rich aryl compounds with nucleophilic [F-18] fluoride has recently expanded with radio-fluorination 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. |
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| AbstractList | The field of labeling electron-rich aryl compounds with nucleophilic [F-18] fluoride has recently expanded with radio-fluorination 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. |
| Author | Kristensen, Jesper Langgaard Petersen, Ida Nymann Herth, Matthias Manfred |
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| Cites_doi | 10.3390/molecules20010470 10.1039/c6sc00197a 10.1016/j.jfluchem.2010.04.004 10.1021/jo800727s 10.1002/anie.201404436 10.1002/anie.201505927 10.1021/ol501243g 10.1021/ja3084797 10.1039/c6cc03295h 10.1021/ol052633u 10.2967/jnumed.114.151332 10.1002/jlcr.1853 10.1002/ejoc.201600705 10.1021/acs.orglett.5b02875 10.3390/molecules16097621 10.1021/jm400770g 10.1002/chem.201405586 10.1021/acs.joc.5b02332 10.1126/science.1212625 10.1021/ja066850h 10.1039/c4ra00674g 10.1038/ncomms5365 10.1021/jm400156p 10.1021/ja409748m |
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| Keywords | DESIGN RADIOFLUORINATION ARENES F-18-FLUORINATION FLUORINATION SALTS FLUORIDE POSITRON-EMISSION-TOMOGRAPHY ARYL HALIDES Comparative studies Nucleophilic substitution Spiro compounds Ylides BORYLATION Isotopic labeling |
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| Title | Nucleophilic F-18-Labeling of Spirocyclic Iodonium Ylide or Boronic Pinacol Ester Precursors: Advantages and Disadvantages |
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