Grignard reactions in imidazolium ionic liquids

I&EC 133

Scott T Handy, shandy@mtsu.edu, Department of Chemistry, Middle Tennessee State University, Box 68, Murfreesboro, TN 37132
Room temperature ionic liquids (RTILs) have gained a great deal of attention as interesting and potentially green solvents for a variety of applications, including organic synthesis. Indeed, virtually every type of reaction imaginable has been conducted in RTILs, with one major exception – alkali metal organometallic reagents. As part of an effort directed at the preparation of more base-stable imidazolium-based RTILs, we have discovered that 2-isopropyl substituted compounds are not only base-stable, but can also be used as recyclable solvents for Grignard and organolithium additions to carbonyl compounds. These results and their implications in synthesis will be discussed.