Copper-Catalyzed Oxidative Cleavage of Electron-Rich Olefins in Water at Room Temperature
| Autor: | Daniel J. Lippincott, Bruce H. Lipshutz, Fabrice Gallou, Pedro J. Trejo-Soto |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Chemical substance Ozonolysis 010405 organic chemistry Chemistry Alkene Organic Chemistry 010402 general chemistry Cleavage (embryo) 01 natural sciences Biochemistry Enol 0104 chemical sciences Catalysis Metal chemistry.chemical_compound visual_art Polymer chemistry visual_art.visual_art_medium Physical and Theoretical Chemistry Alkyl |
| Zdroj: | Organic Letters. 20:5094-5097 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.8b01883 |
| Popis: | A copper-catalyzed oxidative cleavage of electron-rich olefins into their corresponding carbonyl derivatives is described as an alternative to ozonolysis. The scope includes various precursors to aryl ketone derivatives, as well as oxidations of enol ethers bearing atypical alkyl and dialkyl substitution, the first of their kind among such metal catalyzed alkene cleavage reactions. The use of an inexpensive copper salt, room temperature conditions, an aerobic atmosphere, and water as the global reaction medium highlight the green features of this new method. Associated mechanistic investigations are also presented. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|