Enantioselective Cross‐Exchange between C−I and C−C σ Bonds
| Autor: | Xing-Ben Wang, Qian‐Qian Chen, Feng-Na Sun, Zheng Xu, Jian Cao, Li-Wen Xu, Yu-Li Sun |
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| Rok vydání: | 2019 |
| Předmět: |
inorganic chemicals
chemistry.chemical_classification 010405 organic chemistry Chemistry Aryl Iodide General Medicine General Chemistry 010402 general chemistry 01 natural sciences Oxidative addition Medicinal chemistry Catalysis Reductive elimination 0104 chemical sciences Stereocenter chemistry.chemical_compound Intramolecular force Bond cleavage Alkyl |
| Zdroj: | Angewandte Chemie International Edition. 58:6747-6751 |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.201902029 |
| Popis: | A palladium-catalyzed enantioselective intramolecular σ-bond cross-exchange between C-I and C-C bonds is realized, providing chiral indanones bearing an alkyl iodide group and an all-carbon quaternary stereocenter. Pd/TADDOL-derived phosphoramidite is found to be an efficient catalytic system for both C-C bond cleavage and alkyl iodide reductive elimination. In addition to aryl iodides, aryl bromides can also be used for this transformation in the presence of KI. Density-functional theory (DFT) calculation studies support the ring-opening of cyclobutanones occuring through an oxidative addition/reductive elimination process involving PdIV species. |
| Databáze: | OpenAIRE |
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