Iridium-catalyzed regiospecific allylation of dimethyl malonate in ionic liquids
Kabro, AA; Lyubimov, SE; Maksimova, MG; Moiseev, SK; Gavrilov, KN; Kalinin, VN
| HERO ID | 4936260 |
|---|---|
| In Press | No |
| Year | 2007 |
| Title | Iridium-catalyzed regiospecific allylation of dimethyl malonate in ionic liquids |
| Authors | Kabro, AA; Lyubimov, SE; Maksimova, MG; Moiseev, SK; Gavrilov, KN; Kalinin, VN |
| Journal | Russian Chemical Bulletin |
| Volume | 56 |
| Issue | 3 |
| Page Numbers | 540-542 |
| Abstract | Allylation of dimethyl malonate with 1-(4-chlorophenyl)prop-2-enyl methyl carbonate in the presence of [Pd(All)Cl](2), [Rh(COD)Cl](2), [Ir(COD)Cl](2) (COD is cycloocta-1,5-diene), and a chiral ferrocenyl-containing phosphite ligand based on (R)-BINOL (BINOL is 2,2'-dihydroxy-1,1'-binaphthyl) in CH2Cl2 gave a mixture of linear and branched cross-coupling products, the latter having a moderate optical purity (below 51%). The rhodium-and iridium-catalyzed reactions were very highly regioselective (regiospecific in the case of Ir), giving a branched product. In ionic liquids ([bmim][BF4] and [bdmim][BF4]) (bmim is 1-butyl-3-methylimidazolium and bdmim is 1-butyl-2,3-dimethylimidazolium), the Ir-catalyzed reaction regiospecifically afforded a branched product as a racemate. The same result was obtained with [Ir(COD)Cl](2) as a catalyst; this reaction easily occurred in ionic liquids even without a base. |
| Doi | 10.1007/s11172-007-0086-0 |
| Wosid | WOS:000248857600024 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | ionic liquid; allylation; metal complex catalysis; iridium; rhodium; palladium |