Recent Advances in Pd‐Catalyzed Cross‐Coupling Reaction in Ionic Liquids

Li, Jianxiao; Yang, Shaorong; Wu, Wanqing; Jiang, Huanfeng

doi:10.1002/ejoc.201701509

Cited by 100 publications

(42 citation statements)

References 160 publications

(94 reference statements)

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“…Satisfactorily,w hen HOAc (1.5 mL) and DMF (0.5 mL) were used as co-solvents, the 4-vinyl substituted isoxazole derivatives could be successfully produced (Scheme 8). [25] Similarly,a wide range of functional groupso fa lkynone O-methyloximes (14)i ncorporating alkyl, aryl, heteroaryl, halo and vinyl functionalities were compatible with the developed conditions, giving 4-alkenylation isoxazoles (16)i ng ood to excellent yields. However,t he aliphatic alkyne was not compatible with the present catalytic system,a nd no desired product 16 e was detected.…”

Section: Introductionmentioning

confidence: 92%

“…Combining this with our interest in palladium‐catalyzed transformations of unsaturated hydrocarbon, we reviewed the application of the ionic liquids as the green solvent for palladium‐catalyzed alkynes and/or alkenes coupling reaction for the preparation of diverse heterocyclic frameworks in 2016 . Recently, we also illustrated the most important achievements in palladium‐catalyzed coupling approaches with ionic liquids as the irreplaceable solvents . In this Minireview, we described the recent advances on the palladium‐catalyzed cascade cyclization/ alkynylation from 2005 to the beginning of 2019, including our recent contributions.…”

Section: Introductionmentioning

confidence: 99%

“…[15] Recently,w ea lso illustrated the most important achievements in palladium-catalyzed coupling approachesw ith ionic liquidsa st he irreplaceable solvents. [16] In this Minireview,w ed escribed the recent advances on the palladium-catalyzed cascade cyclization/ alkynylation from 2005 to the beginning of 2019, including our recent contributions. This Minireview is mainly organized accordingt ot he following reactiont ypes:t he oxypalladation initiated cascade cyclization, aminopalladation-initiated cascade cyclization,i ntramolecular Heck-type cascade cyclization, carbocyclizations cascade cyclization, and other types of cascade cyclization reaction.…”

Section: Introductionmentioning

confidence: 99%

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Palladium‐Catalyzed Cascade Cyclization/Alkynylation Reactions

Yang

et al. 2019

Chemistry An Asian Journal

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Palladium‐catalyzed cascade cyclization reactions have witnessed significant improvements in recent years. Among them, palladium‐catalyzed cascade cyclization/alkynylation are especially attractive, which can assemble structurally diverse monocyclic, bicyclic, fused polycyclic, and spirocyclic skeletons with excellent chemoselectivities. In this Minireview, palladium‐catalyzed cascade cyclization/alkynylation have been summarized and discussed in detail with focus on oxypalladation and aminopalladation‐initiated cascade cyclization, intramolecular Heck‐type cascade cyclization, carbocyclizations, cascade cyclizations, and other types of cascade cyclization reactions. Some significant and representative synthetic methodologies and their synthetic applications and reaction mechanisms have also been described.

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Section: Introductionmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Palladium‐Catalyzed Cascade Cyclization/Alkynylation Reactions

Yang

et al. 2019

Chemistry An Asian Journal

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“…Ionic liquids have a broad range of industrial properties, and research in the field of ILs endures to witness an astonishing period of remarkable growth. The importance of ionic liquids increases due to their use in synthesis as new solvents, as well as in the process of bio-catalysis, catalysis, chemical engineering and material science [1][2][3][4][5]. Nowdays, ultrasonic measurements have captured more importance in the field of industries, medical science engineering and agriculture.…”

Section: Introductionmentioning

confidence: 99%

Ultrasonic studies on temperature dependence of ion solvent interactions of ionic liquid 1-butyl-2,3- dimethylimidazolium chloride in aqueous solutions of tetra-n-butylammonium bromide at T = (298.15 to 313.15) K

2020

Biointerface Res Appl Chem

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The densities (ρ), and ultrasonic velocities (u) of 1-Butyl-2, 3-dimethylimmidazolium chloride [ ] in aqueous solutions of Tetran-butyl ammonium bromide over the complete range of concentrations has been calculated at different temperatures T= (298.15 to 313)K. Experimentally obtained values of ρ and u were used to calculate the parameters like acoustic impedance (Z), isentropic compressibility (β S ), molar sound velocity (Rao's constant) (R), molar compressibility (Wada's constant)(W), intermolecular free length (L f ), co-efficient of thermal expansion (α), heat capacity ratio (γ), isothermal compressibility (β T ) and nonlinearity parameters (B/A). The final results obtained were analyzed to understand the ion-solvent and ion-ion interaction so taking place in the solutions. Further, the effect of temperature on the ion solvent interactions was discussed. Ion-solvent interactions are affected by the thermo acoustical properties and by nonlinear parameters. Keywords: Ion-solvent interactions; Tetra-n-butyl ammonium bromide; 1-Butyl-2,3-dimethyl imidazolium chloride; Wada's constant; Rao's constant; ultrasonic velocity. MATERIALS AND METHODS Materials.The ionic liquid, 1-Butyl-2,3-dimethylimidazolium chloride, [ ] , with mass fraction purity ≥ 0.985, Tetra-nbutyl ammonium bromide, TBAB with mass fraction purity ≥ 0.99 were imported from Sigma-Aldrich (U.S.A.). The IL,[ ] , was dried overnight to eliminate moisture content under vacuum at 343.15 K. Later than Karl Fischer analysis, the water content was found to be 351ppm. Tetra butyl ammonium bromide was purified by recrystallization from acetone, and all the required substances were desiccated by keeping in vacuum desiccators over for about 2-3 days before its application. The complete information of the compounds taken in this study is presented in Table 1. Instruments and methods.Electronic balance of model ABJ-220-4NM (KERN, Germany) was used to record the mass of solute and solvents with a precision of 10 -4 g. The solutions of concentration 0.08, 0.10, and 0.12mol dm -3 were prepared by weighing the required amount of electrolyte in a weighing bottle and then dissolving it in the required amount of solvent in a 250 mL measuring flask. Rest of the solutions of concentration 0.001, 0.005, 0.01, 0.02, 0.04, and 0.06 mol dm -3 were prepared by dilution. The conversion of

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“…[15] Recently,w eh ave successfully developed ap alladium-catalyzed regioselective threecomponent cascadeb isthiolation of terminal alkynes by using ionic liquidsa st he additive. [16] Inspired by our long-standing interesti ne co-friendly chemistry [17] and Pd-catalyzedc rosscoupling reactions for the construction of structurally diverse heterocyclic frameworks, [18] herein we describe an efficient and practical NHC-palladium-catalyzed three-component cascade cyclization/alkynylation in ionic liquids(Scheme 1b).…”

Section: Introductionmentioning

confidence: 99%