Organocatalyzed Birch Reduction Driven by Visible Light
| Autor: | Chern-Hooi Lim, Dian-Feng Chen, Garret M. Miyake, Max Kudisch, Justin P. Cole, Ryan M. Pearson |
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| Rok vydání: | 2020 |
| Předmět: |
Light
Imides 010402 general chemistry Photochemistry Solvated electron 01 natural sciences Biochemistry Article Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Cyclohexenes Benzene Derivatives Molecule Reactivity (chemistry) Benzene Perylene Birch reduction Molecular Structure Photoredox catalysis General Chemistry Photochemical Processes Alkali metal 0104 chemical sciences chemistry Organocatalysis Oxidation-Reduction Visible spectrum |
| Zdroj: | J Am Chem Soc |
| DOI: | 10.26434/chemrxiv.11860221.v1 |
| Popis: | The Birch reduction is a powerful synthetic methodology that uses solvated electrons to convert inert arenes to 1,4-cyclohexadienes—valuable intermediates for building molecular complexity. Birch reductions traditionally employ alkali metals dissolved in ammonia to produce a solvated electron for the reduction of unactivated arenes such as benzene (E(red) < −3.42 V vs SCE). Photoredox catalysts have been gaining popularity in highly reducing applications, but none have been reported to demonstrate reduction potentials powerful enough to reduce benzene. Here, we introduce benzo[ghi]perylene imides as new organic photoredox catalysts for Birch reductions performed at ambient temperature and driven by visible light from commercially available LEDs. Using low catalyst loadings ( |
| Databáze: | OpenAIRE |
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