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Palladium‐Catalyzed Dearomative syn ‐1,4‐Carboamination with Grignard Reagents
| Content Provider | Scilit |
|---|---|
| Author | Tang, Conghui Okumura, Mikiko Zhu, Yunbo Hooper, Annie R. Zhou, Yu Lee, Yu‐Hsuan Sarlah, David |
| Copyright Year | 2019 |
| Description | Journal: Angewandte Chemie International Edition A protocol for palladium‐catalyzed dearomative functionalization of simple, nonactivated arenes with Grignard reagents has been established. This one‐pot method features a visible‐light‐mediated [4+2] cycloaddition between an arene and an arenophile, and subsequent palladium‐catalyzed allylic substitution of the resulting cycloadduct with a Grignard reagent. A variety of arenes and Grignard reagents can participate in this process, forming carboaminated products with exclusive syn‐1,4‐selectivity. Moreover, the dearomatized products are amenable to further elaborations, providing functionalized alicyclic motifs and pharmacophores. For example, naphthalene was converted into sertraline, one of the most prescribed antidepressants, in only four operations. Finally, this process could also be conducted in an enantioselective fashion, as demonstrated with the desymmetrization of naphthalene. |
| Related Links | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6640109/pdf |
| Ending Page | 10249 |
| Page Count | 5 |
| Starting Page | 10245 |
| ISSN | 14337851 |
| e-ISSN | 15213773 |
| DOI | 10.1002/anie.201905021 |
| Journal | Angewandte Chemie International Edition |
| Issue Number | 30 |
| Volume Number | 58 |
| Language | English |
| Publisher | Wiley-Blackwell |
| Publisher Date | 2019-05-15 |
| Access Restriction | Open |
| Subject Keyword | Journal: Angewandte Chemie International Edition Organic Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Chemistry Catalysis |
