Organic synthesis in fluoroalcohol-water two-phase systems
| Autor: | Nathaniel Weisner, Morteza G. Khaledi |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Aqueous solution
010405 organic chemistry Product recovery Inorganic chemistry Aqueous two-phase system 010402 general chemistry 01 natural sciences Pollution 0104 chemical sciences chemistry.chemical_compound Benzyl chloride Nucleophile chemistry Phase (matter) Electrophile Environmental Chemistry Organic chemistry Organic synthesis |
| Zdroj: | Green Chemistry. 18:681-685 |
| ISSN: | 1463-9270 1463-9262 |
| Popis: | The addition of organic reactants to aqueous solutions of hexafluoroisopropanol (HFIP) leads to the formation of a two-phase system with one phase enriched in HFIP and the organic reactant and another largely aqueous phase. These systems were used as a reaction medium for Friedel–Crafts reactions between arenes and heteroarenes with a benzyl chloride electrophile. Good to excellent yields were obtained for nucleophiles of varying strength in the presence of large amounts of water (10–20 % HFIP v/v), which is unusual for weaker nucleophiles. Surprisingly, the reactions performed in the two-phase systems outperformed those in pure (100%) HFIP. The presence of the aqueous phase offers advantages over single-phase reaction media in terms of driving the reaction and product recovery. This system offers a new, largely aqueous medium for organic synthesis. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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