Palladium-catalyzed tandem addition/cyclization in aqueous medium: synthesis of 2-arylindoles
| Autor: | Zhu Jianghe, Shuling Yu, Kun Hu, Tianxing Cheng, Zhang Yetong, Jiuxi Chen, Julin Gong, Qi Linjun |
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| Rok vydání: | 2017 |
| Předmět: |
Nucleophilic addition
Aqueous medium Tandem 010405 organic chemistry Chemistry Organic Chemistry Intramolecular cyclization chemistry.chemical_element 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Catalysis Organic chemistry Physical and Theoretical Chemistry Palladium |
| Zdroj: | Organicbiomolecular chemistry. 15(20) |
| ISSN: | 1477-0539 |
| Popis: | An efficient protocol to construct 2-arylindoles was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover, the utility of this catalytic tandem transformation was also demonstrated in an efficient gram-scale synthesis. This method provides an alternative synthetic tool for accessing a more diverse array of 2-arylindoles. |
| Databáze: | OpenAIRE |
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