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Selective C–O bond formation via a photocatalytic radical coupling strategy: access to perfluoroalkoxylated (ORF) arenes and heteroarenes† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01684k Click here for additional data file.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Lee, Johnny W. Spiegowski, Dominique N. Ngai, Ming-Yu |
| Copyright Year | 2017 |
| Abstract | Development of an efficient process that employs commercially available and cost effective reagents for the synthesis of perfluoroalkoxylated aromatic compounds (Ar-ORF) remains a daunting challenge in organic synthesis. Herein, we report the first catalytic protocol using readily available perfluoroalkyl iodides (RFI) and N-(hetero)aryl-N-hydroxylamides to access a wide range of perfluoroalkoxylated (hetero)arenes. Mild reaction conditions allow for selective O-RF bond formation over a broad substrate scope and are tolerant of a wide variety of functional groups. Mechanistic studies suggest the formation and recombination of persistent N-hydroxyl radicals and transient RF radicals under photocatalytic reaction conditions to generate N-ORF compounds that rearrange to afford the desired products. |
| Starting Page | 6066 |
| Ending Page | 6070 |
| Page Count | 5 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c7sc01684k |
| Alternate Webpage(s) | https://pubs.rsc.org/en/Content/ArticlePDF/2017/SC/C7SC01684K |
| PubMed reference number | 28989637 |
| Alternate Webpage(s) | https://doi.org/10.1039/c7sc01684k |
| Journal | Medline |
| Volume Number | 8 |
| Journal | Chemical science |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
