Copper-free and amine-free Sonogashira coupling in air in a mixed aqueous medium by palladium complexes of N/O-functionalized N-heterocyclic carbenes

Samantaray, Manoja K.; Shaikh, Mobin M.; Ghosh, Prasenjit

doi:10.1016/j.jorganchem.2009.06.026

Cited by 67 publications

(23 citation statements)

References 92 publications

(97 reference statements)

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“…[6][7][8] For instance, organopalladium complexes, which have been widely used to catalyze various C-C bond coupling reactions such as the Sonogashira, Heck, and Suzuki reactions, [9][10][11][12][13][14][15][16][17][18] can be tethered onto the surface amine groups of primary amine-functionalized mesoporous silica. These organopalladium complexes can also be supported on mesoporous materials by means of other ligands such as phosphanes and diamines.…”

Section: Introductionmentioning

confidence: 99%

Bifunctional Mesoporous Silica Catalyst for C–C Bond Forming Tandem Reactions

et al. 2011

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We report on the synthesis and catalytic properties of a class of hybrid organic-inorganic mesoporous bifunctional heterogeneous catalysts for efficient catalysis of two-step tandem reactions in one pot. With a solvent-assisted grafting method, two different catalytic groups, that is, an organoamine and a palladium-organodiamine complex, were immobilized onto high-surface-area mesoporous silica sequentially, by using their corresponding organosilanes in 2-propanol or toluene as the solvent in the first step and toluene as the solvent in the second step. Both MCM-41 and SBA-15 mesoporous silicas were used as support materials for the two catalytic groups, and the effect of different sequential grafting of the two organosilanes in 2-propanol or toluene on the structures and the catalytic properties of the resulting bifunctional catalysts were investigated. By using the resulting amine/Pd IIdiamine bifunctional mesoporous material as catalyst, the occurrence of two very important C-C bond forming reactions,

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Section: Introductionmentioning

confidence: 99%

Bifunctional Mesoporous Silica Catalyst for C–C Bond Forming Tandem Reactions

et al. 2011

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“…Moreover, the use of a copper reagent results in contamination of the coupling products with metal residues. Thus a lot of efforts are underway toward developing new palladium catalysts and copper-and amine-free conditions for the Sonogashira reaction [23][24][25][26]. Among them, a wide variety of palladacycles have been reported and successfully used in the Sonogashira reaction [5,[27][28][29][30].…”

Section: Application In Sonogashira Reactionmentioning

confidence: 99%

Synthesis and Characterization of Triphenylphosphine Adducts of Ferrocene-Based Palladacycles and Their Performance in the Suzuki and Sonogashira Reactions with Bromo- and Chloroarenes

Bai

et al. 2012

Molecules

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Abstract:A new triphenylphosphine adduct of cyclopalladated ferrocenylpyridazine containing a chloride anion, 2a, has been synthesized from the reaction of the chloride-bridged palladacyclic dimer 1a with triphenylphosphine. The corresponding adducts 3a,b containing iodide anion have been readily prepared through anion exchange reactions of 2a,b with NaI in acetone. These complexes were characterized by elemental analysis, IR and 1 H-NMR. Additionally, their crystal structures have been determined by X-ray diffraction and intermolecular C-H···X (Cl, Br, I) bonds were found in the crystals. The use of these palladacycles as catalysts for the Suzuki and Sonogashira reactions was examined. The complexes 2a,b exhibited higher catalytic activity than the corresponding 3a,b in the Suzuki reaction. However, the order of activity of adducts with varying halogen anions is 3a~3b > 2a~2b in the Sonogashira reaction.

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“…A Pd(II) complex containing an imido-functionalized NHC was synthesized by Ghosh et al Complex 11 was applied for Sonogashira reaction under copper-free and amine-free conditions in air and in a mixed aqueous medium (Chart 4) [13]. In this case, excellent yields were achieved regardless of the electronic character of the starting materials by using 3 mol % catalyst loadings.…”

Section: Bidentate Nhc Ligands Containing One N-donating Atommentioning

confidence: 99%

Potentially Hemilabile N-Heterocyclic Carbene Palladium Complexes: Synthesis and Catalytic Applications

Gu¹,

Chen

Qiu³

et al. 2011

COC

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Palladium complexes containing hemilabile N-heterocyclic carbene (NHC) ligands have become a promising family of complexes due to an excellent balance between stability and reactivity that enables them to catalyze a wide range of organic reactions. This review will focus on the palladium complexes of hemilabile NHC ligands, especially their synthesis and catalytic applications in organic transformations. This article is organized in the following categories according to the additional donating atoms: i) Synthesis and catalytic applications of Pd complexes containing bidentate CE (E = N, O, S, or P) ligands, ii) Synthesis and catalytic applications of Pd complexes containing tridentate CE2 (E = N, O, S, or P) ligands, iii) Synthesis and catalytic applications of Pd complexes containing tridentate C2N ligands, iv) Synthesis and catalytic applications of Pd complexes containing tridentate CNO type ligands, and (V) Synthesis of Pd complexes containing tetradentate C2N2 ligands.

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Copper-free and amine-free Sonogashira coupling in air in a mixed aqueous medium by palladium complexes of N/O-functionalized N-heterocyclic carbenes

Cited by 67 publications

References 92 publications

Bifunctional Mesoporous Silica Catalyst for C–C Bond Forming Tandem Reactions

Bifunctional Mesoporous Silica Catalyst for C–C Bond Forming Tandem Reactions

Synthesis and Characterization of Triphenylphosphine Adducts of Ferrocene-Based Palladacycles and Their Performance in the Suzuki and Sonogashira Reactions with Bromo- and Chloroarenes

Potentially Hemilabile N-Heterocyclic Carbene Palladium Complexes: Synthesis and Catalytic Applications

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