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 |
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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 |