Indium-Mediated Allylation of Carbonyl Compounds in Ionic Liquids: Effect of Salts in Ionic Liquids

Molecules

Yuji Takagi¹  Tsunehisa Hirashita¹  Shuki Araki¹  Takayuki Noda¹  Fusako Takahashi¹ 

[1] Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan;

关键词: indium;    allylation;    ionic liquids;    carbonyl compounds;    homoallylic alcohols;   

DOI  :  10.3390/molecules23071696

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown