The 2-position of imidazolium cations is known to be relatively acidic, leading to the useful Arduengo-type carbenes. At the same time, the acidity of this site can lead to undesired side reactions when using imidazolium-based ionic liquids as solvents. In this note, we describe the surprisingly facile deuterium exchange at this position and also the synthesis and exchange under modestly basic conditions (triethylamine) of a series of 2-methyl-substituted compounds.
Room temperature ionic liquids (RTILs) have attracted a great deal of interest as environmentally benign (green) solvents for organic synthesis. More recently, RTILs that are chiral, less expensive, or functionalized (protic or Lewis basic) have been developed. In many cases, these new solvents are based on the modification of natural products. This paper is an overview of these new biorenewable RTILs.
A simple guide for predicting the order and site of coupling (Suzuki, Stille, Negishi, Sonogashira, etc.) in polyhaloheteroaromatics based upon the (1)H NMR chemical shift values of the parent non-halogenated heteroaromatics has been developed.
[reaction: see text] Fructose has been used as the starting material for the preparation of a new class of room-temperature ionic liquids (RTILs). These liquids exhibit tunable solvent properties much like conventional imidazole-based RTILs. They have been applied as recyclable solvents for the Heck reaction of aryl iodides.
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