α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles
| Autor: | Matheus Pereira de Jesus, Clarice Alves Dale Caiuby, Antonio C. B. Burtoloso |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Imidoyl chloride 010405 organic chemistry Organic Chemistry chemistry.chemical_element One-Step 010402 general chemistry 01 natural sciences Medicinal chemistry Sulfur 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Ylide Yield (chemistry) Iridium Lewis acids and bases QUÍMICA ORGÂNICA |
| Zdroj: | Repositório Institucional da USP (Biblioteca Digital da Produção Intelectual) Universidade de São Paulo (USP) instacron:USP |
| ISSN: | 1520-6904 |
| Popis: | Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield). |
| Databáze: | OpenAIRE |
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