First C−H Activation Route to Oxindoles using Copper Catalysis
| Autor: | David S. Pugh, Alexis Perry, Johannes E. M. N. Klein, Richard J. K. Taylor |
|---|---|
| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
Indoles Molecular Structure Base (chemistry) Organic Chemistry chemistry.chemical_element Total synthesis Biochemistry Copper Toluene Catalysis Oxindoles chemistry.chemical_compound Horsfiline chemistry Organic chemistry Anilides Spiro Compounds Oxindole Physical and Theoretical Chemistry Oxidation-Reduction Mesitylene |
| Zdroj: | Organic Letters. 12:3446-3449 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol1012668 |
| Popis: | The preparation of 3,3-disubstituted oxindoles by a formal C-H, Ar-H coupling of anilides is described. Highly efficient conditions have been identified using catalytic (5 mol %) Cu(OAc)(2).H(2)O with atmospheric oxygen as the reoxidant; no additional base is required, and the reaction can be run in toluene or mesitylene. Optimization studies are reported together with a scope and limitation investigation based on variation of the anilide precursors. The application of this methodology to prepare a key intermediate for the total synthesis of the anticancer, analgesic oxindole alkaloid Horsfiline is also described. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|