Continuous-flow photo-induced decarboxylative annulative access to fused imidazole derivatives via a microreactor containing immobilized ruthenium
| Autor: | Niraj Kumar Vishwakarma, Praveen Reddy Adiyala, Yoon-Ho Hwang, Dong-Pyo Kim, Seungwook Jang |
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| Rok vydání: | 2020 |
| Předmět: |
Annulation
Polydimethylsiloxane 010405 organic chemistry Decarboxylation Continuous flow chemistry.chemical_element 010402 general chemistry 01 natural sciences Pollution Fluorescence Combinatorial chemistry 0104 chemical sciences Ruthenium chemistry.chemical_compound chemistry Environmental Chemistry Imidazole Microreactor |
| Zdroj: | Green Chemistry. 22:1565-1571 |
| ISSN: | 1463-9270 1463-9262 |
| Popis: | Visible-light-driven continuous-flow decarboxylative annulation was achieved and used along with a microreactor containing immobilized ruthenium catalyst to construct valuable fused imidazole derivatives with high yields under an open atmosphere. Notably, this chemistry included the use of L-proline and α-azidochalcone as precursors of an α-amino radical and 2H-azirine via photo-induced decarboxylation and denitrogenation, respectively, to give the annulated imidazole derivatives as a result of the formation of two new C–N bonds. Moreover the novel, environmentally benign and efficient continuous-flow protocol was further improved by carrying out the reaction in a polydimethylsiloxane (PDMS) microreactor with immobilized Ru3+ under fluorescent or white LED light, enabling excellent yields (70–94%) at a reaction time (2 min) significantly shorter than that (16 h) of the batch protocol. |
| Databáze: | OpenAIRE |
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