Silylstannations of α,β-unsaturated carbonyl compounds via the generation of Bu3Sn– in ionic liquids

Abstract

The tributylstannyl anion, Bu3Sn-, can be generated in imidazolium based ionic liquids from Me3SiSnBu3 and reacted with alpha,beta-unsaturated carbonyl compounds to afford 3-tributylstannylated products in good yields.

Catalysis in Ionic Liquids

“…The tributylstannyl anion, Bu 3 Sn 2 , can be generated in 1,3dialkylimidazolium-based ILs from Me 3 SiSnBu 3 and reacted with R,β-unsaturated carbonyl compounds (cyclohex-2-en-1-one, cyclopent-2-en-1-one, trans-4-phenyl-3-buten-2-one) to afford 3-tributylstannylated products in good yields (Scheme 38). 321 As shown in many reactions, the choice of cation and anion is found to affect the yields obtained. Lower yields of 3-tributylstannylcyclohexanone were obtained using [C 4 mim][BF 4 ] compared with [C 4 mim]Cl even after extended reaction times and use of elevated temperatures.…”

Metal Chelate Formation Using a Task-Specific Ionic Liquid

“…Ionic liquids that have been “designed” to perform a desired function are referred to as task-specific ionic liquids (TSILs) . TSILs that perform a variety of functions ranging from those that act as a catalyst and reactant to those that are specifically designed to sequester CO 2 gas have been prepared . As alluded to above, ionic liquids have also been used to extract a variety of chemical species from the solution phase.…”