Piperidine-appended imidazolium ionic liquid as task-specific basic-IL for Suzuki and Heck reactions and for tandem Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck protocols

Palladium Catalyzed Electrophilic C2‐Arylation of Azoles by Aryltriazenes in Ionic Liquid Promoted by Acidic Ionic Liquid

“…Thus, in an endeavor to overcome these limitations, a greener synthetic protocol towards the access of the target molecule is conceived by the use of ionic liquids as a reaction medium/promoter mainly due to its environmental acceptability. In our long pursuit of developing sustainability and greener strategies, we have established green synthetic methodologies employing ionic liquids as solvent or catalyst for the synthesis of benzoxazole and benzothiazoles and metal‐mediated cross‐coupling reactions exploiting 1‐aryltriazenes as a coupling partner. With these previous knowledge, we report herein the base/ligand free and open‐air Pd/Cu catalyzed arylation of azoles at C2 position with three different 1‐aryltriazenes as coupling partner instead of a single triazene reagent that reported elsewhere …”

A Combination of Biocompatible Room Temperature Ionic Liquid and Palladium Catalyst for Base‐ and Ligand‐Free Suzuki Coupling Reactions

“…To accomplish this goal, researchers have adopted a main strategy of anchoring Pd‐catalysts onto the surface of solid supports such as magnetic particle MMT K 10, Merrifield resin, magnetic nanoparticles, and organosilica with the aid of an IL. In a recent example, Kalkhambkar et al reported a Suzuki–Miyaura reaction with a specially designed basic IL, a piperidine‐appended imidazolium IL, along with 1‐butyl‐3‐mehylimidazolium hexafluorophosphate ([BMIM][PF 6 ]) as a solvent …”

“…In a recent example, Kalkhambkar et al reported a Suzuki-Miyaura reaction with a specially designed basic IL, a piperidine-appended imidazolium IL, along with 1-butyl-3-mehylimidazolium hexafluorophosphate ([BMIM][PF 6 ]) as a solvent. [11] Despite the impressive growth in the combination of metalcatalysts and greener reaction media over the past few decades, the development of a highly efficient Pd-catalyst system, especially one that functions in room-temperature Ils, remains as a considerable challenge.…”

3-(Biphenyl)acrylates by One-Pot Suzuki Cross Coupling–Wittig Olefination Reactions

“…Also, methyl 3-(4′methyl[1,1′-biphenyl]-4-yl)acrylate (24) has been prepared by the reaction of p-tolylphenyboronic acid (23) with 4-bromocinnamic acid and with 4-chlorocinnamic acid, followed by a subsquent esterification [13]. Ethyl 3-([1,1′-biphenyl]-4-yl)acrylate and ethyl 3-(3′-methyl[1,1′-biphenyl]-4yl)acrylate have also been prepared by one-pot Suzuki-Horner-Emmons reaction in an ionic liquid protocol, where, however, the arylboronic acid could only be introduced after the Horner Emmons reaction was complete [14]. We have published some prior work on the Suzuki cross-coupling-Wittig olefination, also to biphenylacrylates [6].…”

“…Scheme 2. Suzuki-cross-coupling/Wittig olefination one pot transformation to methyl 3-(biphenyl)acrylates (2) using 4-bromophenylboronic acid (14) the central building block.…”