Amplification of Trichloroisocyanuric Acid (TCCA) Reactivity for Chlorination of Arenes and Heteroarenes via Catalytic Organic Dye Activation
| Autor: | Amy K. Pitzel, Fares H. Refai, Juan J. Alvarado, Alvaro Tomas Espinosa, David A. Rogers, John L. Hoerr, Angus A. Lamar, Adam T. Bensalah |
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| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Organic Chemistry 010402 general chemistry Phenazone 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Brilliant green Reagent Electrophile Organic dye polycyclic compounds medicine Reactivity (chemistry) Physical and Theoretical Chemistry Trichloroisocyanuric acid medicine.drug |
| Zdroj: | Organic letters. 21(11) |
| ISSN: | 1523-7052 |
| Popis: | Heteroarenes and arenes that contain electron-withdrawing groups are chlorinated in good to excellent yields (scalable to gram scale) using trichloroisocyanuric acid (TCCA) and catalytic Brilliant Green (BG). Visible-light activation of BG serves to amplify the electrophilic nature of TCCA, providing a mild alternative approach to acid-promoted chlorination of deactivated (hetero)aromatic substrates. The utility of the TCCA/BG system is demonstrated through comparison to other chlorinating reagents and by the chlorination of pharmaceuticals including caffeine, lidocaine, and phenazone. |
| Databáze: | OpenAIRE |
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