SN2 fluorination reactions in ionic liquids: a mechanistic study towards solvent engineering
Oh, YH; Jang, HB; Im, S; Song, MJ; Kim, SY; Park, SW; Chi, DY; Song, CE; Lee, S
HERO ID
1070914
Reference Type
Journal Article
Year
2011
Language
English
PMID
| HERO ID | 1070914 |
|---|---|
| In Press | No |
| Year | 2011 |
| Title | SN2 fluorination reactions in ionic liquids: a mechanistic study towards solvent engineering |
| Authors | Oh, YH; Jang, HB; Im, S; Song, MJ; Kim, SY; Park, SW; Chi, DY; Song, CE; Lee, S |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 9 |
| Issue | 2 |
| Page Numbers | 418-422 |
| Abstract | In the catalysis of S(N)2 fluorination reactions, the ionic liquid anion plays a key role as a Lewis base by binding to the counterion Cs(+) and thereby reducing the retarding Coulombic influence of Cs(+) on the nucleophile F(-). The reaction rates also depend critically on the structures of ionic liquid cation, for example, n-butyl imidazolium gives no S(N)2 products, whereas n-butylmethyl imidazolium works well. The origin of the observed phenomenal synergetic effects by the ionic liquid [mim-(t)OH][OMs], in which t-butanol is bonded covalently to the cation [mim], is that the t-butanol moiety binds to the leaving group of the substrate, moderating the retarding interactions between the acidic hydrogen and F(-). This work is a significant step toward designing and engineering solvents for promoting specific chemical reactions. |
| Doi | 10.1039/c0ob00426j |
| Pmid | 20949216 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |
| Is Qa | No |