Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C-C-Coupling Reactions
- The acetamide group enables regioselective oxidative ortho-C-H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles.
| Author details: | Bernd SchmidtORCiDGND, Nelli Elizarov, Uwe SchildeORCiDGND, Alexandra Kelling |
|---|---|
| DOI: | https://doi.org/10.1021/acs.joc.5b00272 |
| ISSN: | 0022-3263 |
| Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/25700158 |
| Title of parent work (English): | The journal of organic chemistry |
| Publisher: | American Chemical Society |
| Place of publishing: | Washington |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2015 |
| Publication year: | 2015 |
| Release date: | 2017/03/27 |
| Volume: | 80 |
| Issue: | 9 |
| Number of pages: | 12 |
| First page: | 4223 |
| Last Page: | 4234 |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
