Photochemical intermolecular dearomative cycloaddition of bicyclic azaarenes with alkenes
| Autor: | Xiaolong Zhang, Felix Schäfer, Kendall N. Houk, Shuming Chen, Arne Heusler, Renyu Guo, Jiajia Ma, M. Kevin Brown, Constantin G. Daniliuc, Peter Bellotti, Frank Glorius |
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| Rok vydání: | 2021 |
| Předmět: |
Diene
General Science & Technology Stereoisomerism Alkenes 010402 general chemistry 01 natural sciences Hydrocarbons Aromatic Catalysis chemistry.chemical_compound Reactivity (chemistry) chemistry.chemical_classification Multidisciplinary Bicyclic molecule Molecular Structure Cycloaddition Reaction 010405 organic chemistry Alkene Combinatorial chemistry Cycloaddition Hydrocarbons 3. Good health 0104 chemical sciences chemistry Energy Transfer Quinolines Selectivity Aromatic |
| Zdroj: | Science (New York, N.Y.), vol 371, iss 6536 Science |
| Popis: | Heteroaromatics lured into cycloadditions The Diels-Alder reaction is widely used to produce six-membered carbon rings from alkenes and dienes. Heteroaromatics such as quinolines resemble dienes in principle, but in practice their pairs of double bonds are inert toward cycloadditions because of aromatic stabilization. Ma et al. report that by using an iridium photosensitizer, they could excite quinolines and related azaarenes to triplet states, thereby disrupting the aromaticity and enabling intermolecular, Diels-Alder–like reactivity toward alkenes (see the Perspective by Schmidt). The reactions proceeded exclusively at the flanking carbons outside the nitrogen-containing ring. Science , this issue p. 1338 ; see also p. 1313 |
| Databáze: | OpenAIRE |
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