Epoxides as Alkylating Reagents for the Catellani Reaction
| Autor: | Qiang Wei, Guangyin Qian, Hong-Gang Cheng, Ruiming Chen, Yuanyuan Xia, Zhi Geng, Han Chen, Chenggui Wu, Qianghui Zhou, Yuming Zhang, Jingyang Zhang |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Aryl Potassium Salt (chemistry) Epoxide chemistry.chemical_element General Medicine General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry XPhos Reagent Catellani reaction |
| Zdroj: | Angewandte Chemie International Edition. 57:3444-3448 |
| ISSN: | 1433-7851 |
| DOI: | 10.1002/anie.201800573 |
| Popis: | We report a cooperative catalytic system comprising a PdII complex, XPhos, and the potassium salt of 5-norbornene-2-carboxylic acid that enables the use of epoxides as alkylating reagents in the Catellani reaction, thereby expanding the existing paradigm of this powerful transformation. The potassium salt of inexpensive 5-norbornene-2-carboxylic acid acts as both mediator and base in the process. This mild, chemoselective, scalable, and atom-economical protocol is compatible with a wide variety of readily available functionalized aryl iodides and epoxides, as well as terminating olefins. The resulting products undergo facile oxa-Michael addition to furnish ubiquitous isochroman scaffolds. |
| Databáze: | OpenAIRE |
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