Nature inspired singlet oxygen generation to access α-amino carbonyl compounds via 1,2-acyl migration
| Autor: | Prakash Kumar Sahoo, Sivaraman Gandhi, Shoubhik Das, Waldemar Schilling, Herbert W. Roesky, Yu Zhang, Samir Kumar Sarkar |
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| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Double bond Photosystem II 010405 organic chemistry Singlet oxygen Biomolecule 010402 general chemistry 7. Clean energy 01 natural sciences Pollution Combinatorial chemistry 0104 chemical sciences Catalysis Chemistry chemistry.chemical_compound chemistry Main group element Environmental Chemistry Reactivity (chemistry) Photosensitizer Engineering sciences. Technology |
| Zdroj: | Green chemistry : cutting-edge research for a greener sustainable future |
| ISSN: | 1463-9270 1463-9262 |
| DOI: | 10.1039/d0gc03555f |
| Popis: | We have discovered chlorophyll catalyzed 1,2-acyl migration reactions to achieve alpha-amino carbonyl compounds directly from the enaminones. In general, singlet oxygen is generated during photosynthesis in the photosystem II center. This singlet oxygen can readily react with the unsaturated double bonds present in biomolecules. This reactivity intrigued us to apply this concept towards unsaturated enaminones and others to achieve highly valuable compounds. Indeed, this photosensitizer is very cheap, commercially available, main group metal based and provided excellent efficiency for singlet oxygen mediated chemistry by achieving high turnover number (TON) > 300 with a high turnover frequency (TOF) of 50 h(-1). Finally, a combination of DFT calculations and detailed mechanistic experiments provided the exact role of the photosensitizer and clear insights into the reaction. |
| Databáze: | OpenAIRE |
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