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A highly site-selective radical sp3 C–H amination of azaheterocycles† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c8sc00590g
| Content Provider | Semantic Scholar |
|---|---|
| Author | Bentley, Keith W. Dummit, Krysta A. Humbeck, Jeffrey F. Van |
| Copyright Year | 2018 |
| Abstract | This report describes the development of a novel C-H amination strategy using both a Cu(ii) Lewis acid and an organic hydrogen atom transfer catalyst to activate benzylic C-H bonds adjacent to aromatic N-heterocycles. This simple methodology demonstrates very high selectivity towards azaheterocycles without using exogenous directing groups and affords excellent site selectivity in substrates with more than one reactive position. A wide range of heterocyclic structures not compatible with previously reported catalytic systems have proven to be amenable to this approach. Mechanistic investigations strongly support a radical-mediated H-atom abstraction, which explains the observed contrast to known closed-shell Lewis acid catalyzed processes. |
| Starting Page | 6440 |
| Ending Page | 6445 |
| Page Count | 6 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c8sc00590g |
| PubMed reference number | 30310574 |
| Journal | Medline |
| Volume Number | 9 |
| Alternate Webpage(s) | https://pubs.rsc.org/en/content/articlepdf/2018/sc/c8sc00590g |
| Alternate Webpage(s) | https://doi.org/10.1039/c8sc00590g |
| Journal | Chemical science |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
