Baylis–Hillman reaction promoted by a recyclable protic-ionic-liquid solvent–catalyst system: DABCO–AcOH–H2O

An Efficient and Recyclable DMAP-Based Ionic Liquid/Water System for Morita–Baylis–Hillman Reactions

“…Note that p-anisaldehyde (4d) previously described as a slow reacting aldehyde in the Morita-Baylis-Hillman reaction was found to give a satisfactory yield after 7 h (Table 2, entry 5). 18,20 To the best of our knowledge, the results shown here are superior to the reported coupling results of both active and less active aromatic aldehydes with acrylate in an ionic liquid alone. It could be suggested that the reason for the reactivity increase in ionic liquid/H 2 O solvent systems could be attributed to the synergistic effect of the polar nature and hydrogen bond formation in a combination of the ionic liquid and water.…”

Protic Ionic Liquids: Evolving Structure–Property Relationships and Expanding Applications

“…Consequently, PILs are a viable alternative as a solvent/ catalyst system where because the PIL is also the catalyst, it enables a very high catalyst concentration, and hence has the potential for faster reaction rates. A series of PILs were prepared from 1,4-diazabicyclic [2,2,2]octane reacted with the Brønsted acids of PhCO 2 H, AcOH, EtCO 2 H, and tert-BuCO 2 H. 544 These PILs were used as the catalyst for the carbon−carbon bond forming Baylis− Hillman reaction in acetonitrile, DMF, methanol, or dioxane as the solvent. The HDABCO-AcO PIL with a small amount of additional water was the best catalyst, for the reaction of aromatic aldehydes, aliphatic aldehydes, and cinnamaldehydes with acrylates or acrylonitrile.…”

Protic Ionic Liquid Promoted One Pot Synthesis of 2‐amino‐4‐(phenyl)‐7‐methyl‐5‐oxo‐4H,5H‐pyrano[4,3‐b]pyran‐3‐carbonitrile Derivatives in Water and Their Antimycobacterial Activity

“…PILs have been reported as the recyclable solvents for the acid catalyzed synthesis of diphenylmethyl thioethers , also reported that the reusability and highly catalytic efficiency for the formylation of amines . DABCO: AcOH: H 2 O solvent ‐ catalyst system also evaluated for the Baylis‐Hillman reaction . Recently, different PILs reported as a recyclable solvent as well as catalyst for the organic syntheses and condensation reactions .…”