Surface-active ionic liquids for palladium-catalysed cross coupling in water: effect of ionic liquid concentration on the catalytically active species

Abstract

We report the design and synthesis of surface-active ionic liquids for application in palladium-catalyzed cross coupling reactions.

Masking specific effects of ionic liquid constituents at the solid–liquid interface by surface functionalization

“…[1][2][3] The assembly of the IL cations and anions at solid-liquid interfaces has been extensively studied, since ion specific effects play a major role in the physico-chemical properties of surfaces immersed in ILs or in their solutions. [4][5][6] The interfacial structure is responsible for reduced friction between surfaces, 7 exfoliation of layered materials 8 and stabilization of various particles in ILs. [9][10][11][12][13] In addition, specific interactions of IL ions with synthetic and natural macromolecules influence the stability of enyzmes, 14 the rate of amyloid fibrillization 15 and phase transition behavior 16 through tailoring the inter and intramolecular forces.…”

New Trends in C–C Cross-Coupling Reactions: The Use of Unconventional Conditions

“…The effects of the IL concentration on the catalytically active species towards Pd-catalyzed cross-coupling reactions was studied by Taskin et al [ 74 ]. A series of surface-active IL were applied as additives in the Heck reaction of ethyl acrylate and iodobenzene, obtaining high yields (> 90%) in water, pointing out the IL concentration as the key factor affecting the formation of the catalytically active species in the reaction, the morphology, and chemical state of the Pd species ( Figure 11 ).…”

“…Conditions: 2 mL (C1 2 mimCl) 1 solution, 0.02 mmol Pd 2 (allyl) 2 Cl 2 , and 0.02 mmol K 2 CO 3 60 min at 80 °C under air. Reproduced with the permission of reference [ 74 ], Copyright 2017 The Royal Society of Chemistry.…”

Palladium Acetate/[CPy][Br]: An Efficient Catalytic System towards the Synthesis of Biologically Relevant Stilbene Derivatives via Heck Cross‐Coupling Reaction.

“…Further exploration of the mixture of tetrabutylammonium acetate and tetrabutylammonium bromide salts as reaction medium for pseudo‐domino protocol for Heck reaction followed by an intramolecular Buchwald–Hartwig reaction was reported by Battistuzzi et al . More recently, Taskin et al . reported the use of surface active ILs for palladium‐catalyzed cross‐coupling reactions in water.…”