Efficient Benzimidazolidinone Synthesis via Rhodium-Catalyzed Double-Decarbonylative C–C Activation/Cycloaddition between Isatins and Isocyanates
| Autor: | Rong Zeng, Guangbin Dong, Peng-hao Chen |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Chemistry Isatin chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Isocyanate Article Catalysis Cycloaddition 0104 chemical sciences Rhodium chemistry.chemical_compound Functional group Organic chemistry Reactivity (chemistry) Curtius rearrangement |
| Zdroj: | ACS Catalysis. 6:969-973 |
| ISSN: | 2155-5435 |
| Popis: | The first decarbonylative cycloaddition of less-strained cyclic ketones (isatins) with isocyanates is reported. Initiated by C-C activation, this distinct [5-2+2] transformation provides a rapid entry to access various benzimidazolidinone derivatives, through which a wide range of isocyanates can be efficiently coupled with broad functional group tolerance. A modified one-pot process, combining Curtius rearrangement and C-C activation, was also achieved by using acyl azides as the starting materials. Detailed mechanistic study revealed a surprising double-decarbonylative reaction pathway. The novel reactivity discovered in this basic research is expected to shed light on developing new heterocycle formation methods through a C-C/isocyanate coupling. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|