The Development of the Metal Coordinated Chiral Ionic Liquids for Purpose of the Application to the Reaction Media

Abstract

Room-temperature ionic liquids (RTILs) are Green Solvent. RTILs have various functions by design and applied as organic reaction solvents, catalysts, electrolytes and extracting agents. We synthesized novel metal coordinated chiral ionic liquids based on S-nicotine. Nicotine is composed a pyridine and a pyrroridine. Selective monoalkylation of the pyridine ring was afforded by using butyl bromide in protic solvent such a methanol. Monoalkylated compound was exchanged anion to BF₄^-, PF₆^- or (CF₃SO₂)₂N^-, and ionic liquid which anion was BF₄^- was miscible with water and which anion were PF₆^- or (CF₃SO₂)₂N^- were immiscible with water.The melting point of all nicotine type ionic liquid showed -35°C or less, especially in the case of (CF₃SO₂)₂N^- was used for the anion, the melting point was -60°C. Nicotinic ionic liquids revealed CD spectrum like a nicotine. There are many examples to take the ionic liquid as reaction solvent and it is expected that the application for these chiral ionic to the enantioselective reaction.