Photoredox‐Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4‐Dihydropyridine Approach
| Autor: | Mikhail O. Konev, Axel Jacobi von Wangelin, Luana Cardinale |
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| Rok vydání: | 2020 |
| Předmět: |
photoredox catalysis
Radical Giese reaction 010402 general chemistry 01 natural sciences Catalysis chemistry.chemical_compound Organic Dyes Reactivity (chemistry) Chemoselectivity 1 4-dihydropyridines chemistry.chemical_classification 010405 organic chemistry Chemistry Alkene Communication Organic Chemistry Photoredox catalysis General Chemistry Combinatorial chemistry Communications 0104 chemical sciences Carboxylation carbamoyl radicals Organic synthesis |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.202002410 |
| Popis: | Functionalization with C1‐building blocks are key synthetic methods in organic synthesis. The low reactivity of the most abundant C1‐molecule, carbon dioxide, makes alternative carboxylation reactions with CO2‐surrogates especially important. We report a photoredox‐catalyzed protocol for alkene carbamoylations. Readily accessible 4‐carboxamido‐Hantzsch esters serve as convenient starting materials that generate carbamoyl radicals upon visible light‐mediated single‐electron transfer. Addition to various alkenes proceeded with high levels of regio‐ and chemoselectivity. Go photo! A photocatalytic carbamoylation of alkenes was developed under mild conditions with a metal‐free catalyst. The reaction utilizes easily available Hantzsch ester derivatives as precursors to carbamoyl radicals which readily add to electron‐deficient alkenes. |
| Databáze: | OpenAIRE |
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