Continuous-flow photo-induced decarboxylative annulative access to fused imidazole derivatives a microreactor containing immobilized ruthenium

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 -prolin...

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Veröffentlicht in:Green chemistry : an international journal and green chemistry resource : GC 2020-03, Vol.22 (5), p.1565-1571
Hauptverfasser: Adiyala, Praveen Reddy, Jang, Seungwook, Vishwakarma, Niraj K, Hwang, Yoon-Ho, Kim, Dong-Pyo
Format: Artikel
Sprache:eng
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Zusammenfassung: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 2 H -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 Ru 3+ 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. Continuous-flow visible-light-induced decarboxylative annulation using a polydimethylsiloxane microreactor containing immobilized Ru 3+ has been established for the construction of fused imidazole derivatives.
ISSN:1463-9262
1463-9270
DOI:10.1039/c9gc03496j