Metal-Oxidant-Free Cobalt-Catalyzed C(sp2)–H Carbonylation of ortho-Arylanilines: An Approach toward Free (NH)-Phenanthridinones
| Autor: | Yaping Lv, Chongren Ai, Chaowei Zhang, Weihui Zhong, Fei Ling |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Diisopropyl azodicarboxylate Organic Chemistry chemistry.chemical_element Total synthesis 010402 general chemistry 01 natural sciences Oxygen Medicinal chemistry 0104 chemical sciences Catalysis Metal chemistry.chemical_compound chemistry visual_art visual_art.visual_art_medium Carbonylation Cobalt Bond cleavage |
| Zdroj: | The Journal of Organic Chemistry. 83:5698-5706 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.8b00730 |
| Popis: | A traceless directing group assisted Co-catalyzed C(sp2)–H carbonylation of ortho-arylanilines for the synthesis of free (NH)-phenanthridinones in metal-based-oxidant-free fashion was accomplished. This protocol employs diisopropyl azodicarboxylate as the CO source and oxygen as the sole oxidant, and provides good yields with various functional tolerance. The methodology has been applied for the total synthesis of PARP inhibitor PJ-34. Furthermore, the kinetic isotopic effect experiments reveal the C–H bond cleavage probably occurred in the rate-determining step. |
| Databáze: | OpenAIRE |
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