Palladium/Norbornene Cooperative Catalysis To Access Tetrahydronaphthalenes and Indanes with a Quaternary Center
| Autor: | Qi Liu, Guangyin Qian, Qianwen Gao, Peng Wang, Qiang Wei, Ze-Shui Liu, Qianghui Zhou, Hong-Gang Cheng |
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| Rok vydání: | 2018 |
| Předmět: |
Annulation
010405 organic chemistry Enantioselective synthesis chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry XPhos Heck reaction Catellani reaction Palladium Norbornene |
| Zdroj: | ACS Catalysis. 8:4783-4788 |
| ISSN: | 2155-5435 |
| DOI: | 10.1021/acscatal.8b00975 |
| Popis: | A cooperative catalytic system comprising a palladium/XPhos complex and 5-norbornene-2-carboxylic acid was developed. This system promotes a two-component annulation reaction, allowing the construction of tetrahydronaphthalenes and indanes that contain quaternary centers through consecutive Catellani-type C–H activation and redox-relay Heck reaction. Inexpensive 5-norbornene-2-carboxylic acid acts as a catalytic mediator (20 mol %) in this process. This mild, scalable, and chemoselective protocol is compatible with a wide variety of readily available aryl iodides and alkylating reagents. Application of this method in a 4-step synthesis of opioid analgesic eptazocine is demonstrated. Preliminary studies underscore the future promise of rendering this Catellani/redox-relay Heck cascade enantioselective. |
| Databáze: | OpenAIRE |
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