Indium-Mediated Allylation of Carbonyl Compounds in Ionic Liquids: Effect of Salts in Ionic Liquids
| Autor: | Takayuki Noda, Yuji Takagi, Shuki Araki, Fusako Takahashi, Tsunehisa Hirashita |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Pharmaceutical Science
indium 010402 general chemistry 01 natural sciences Catalysis Analytical Chemistry ionic liquids lcsh:QD241-441 Crotyl chemistry.chemical_compound homoallylic alcohols lcsh:Organic chemistry Bromide Drug Discovery Polymer chemistry Physical and Theoretical Chemistry Cinchonidine Enantiomeric excess allylation 010405 organic chemistry Communication Organic Chemistry Imidazoles Asymmetric induction 0104 chemical sciences Solvent carbonyl compounds Indium-mediated allylation chemistry Chemistry (miscellaneous) Benzaldehydes Ionic liquid Molecular Medicine Salts Lithium Chloride Palladium |
| Zdroj: | Molecules, Vol 23, Iss 7, p 1696 (2018) Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry |
| ISSN: | 1420-3049 |
| Popis: | The In-mediated allylation of carbonyl compounds can be performed in various types of solvents including ionic liquids. However, we have found that in [bmim][BF4] (where bmim = 1-butyl-3-methylimidazolium), the In-mediated coupling of crotyl bromide with benzaldehyde gives a complex mixture, and some additives, such as halides and amines, are crucial for the successful conversion to the corresponding γ-adduct. Instead, the addition of alcohols or water promotes the formation of the α-adduct. An asymmetric induction with up to 62% enantiomeric excess (ee) was observed employing cinchonidine as an additive in a binary solvent consisting of an ionic liquid and dichloromethane. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|