Reactions and catalytic applications of a PNCNP pincer palladium hydride complex

Chang, Jiarui; Ding, Man; Mao, Jia-Xue; Zhang, Jie; Chen, Xuenian

doi:10.1039/d2dt03131k

Cited by 3 publications

(1 citation statement)

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“…The authors have cited additional references within the Supporting Information. [26][27][28][29][30][31][32][33][34]…”

Section: Supporting Informationmentioning

confidence: 99%

Synthesis and Characterization of Novel Pd@rGO−CuFe₂O₄ Magnetic Nanoparticles: A Recyclable Catalyst for C−C Coupling Reaction in Biomass‐Derived Organic Solvent

Teli,

Reetu,

Singh

et al. 2023

Asian J Org Chem

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Development of new, cost effective, stable heterogeneous catalyst for the organic transformations is an important thematic area of research. Present work describes the development of new Pd@rGO‐CuFe2O4 catalyst and demonstrates its effectiveness for Suzuki‐Miyaura type coupling reactions. The additional advantage of this reaction is its feasibility using biomass‐derived solvent like γ‐Valerolactone (GVL) in aqueous media. The catalyst is prepared hydrothermally and characterized using XRD, FESEM, EDX, and XPS analysis. The catalyst exhibits excellent activity and recyclability (up to six times) in the C‐C coupling reaction to deliver the corresponding biaryl molecules in yields up to 90%. High efficiency for the conversion of nitriles to amides is also revealed by the prepared catalyst.

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“…The authors have cited additional references within the Supporting Information. [26][27][28][29][30][31][32][33][34]…”

Section: Supporting Informationmentioning

confidence: 99%

Synthesis and Characterization of Novel Pd@rGO−CuFe₂O₄ Magnetic Nanoparticles: A Recyclable Catalyst for C−C Coupling Reaction in Biomass‐Derived Organic Solvent

Teli,

Reetu,

Singh

et al. 2023

Asian J Org Chem

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Evaluating the Catalytic Activities of PNCNP Pincer Group 10 Metal Hydride Complexes: Pd-Catalyzed Reduction of CO₂ to the Formic Acid Level with NH₃·BH₃ and NaBH₄ under Ambient Conditions

et al. 2023

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In order to develop efficient protocols for CO 2 reduction with less expensive and more convenient hydrogen sources, the catalytic reactivities of group 10 metal hydride complexes supported by a PNCNP pincer ligand, [2,6-( t Bu 2 PNH) 2 C 6 H 3 ]MH (M = Ni, 1a; Pd, 1b; Pt, 1c), against the hydroboration of CO 2 with NH 3 •BH 3 and NaBH 4 have been explored. Both 1a and 1b readily react with CO 2 at room temperature to form the corresponding formato complexes, [2,6-( t Bu 2 PNH) 2 C 6 H 3 ]MOC(O)H (M = Ni, 2a; Pd, 2b), in nearly quantitative yields. Treatment of NH 3 •BH 3 with CO 2 (1 atm) in 1,4-dioxane or THF at room temperature in the presence of 0.05−1.0 mol % of 1b followed by hydrolysis of the resulting mixtures produces formic acid in 105−186% yields, and initial turnover frequencies of up to 2000 h −1 are observed. In the presence of 1.0 mol % of 1b, NaBH 4 reacts with CO 2 (1 atm) in THF at room temperature to form NaB[OC(O)H] 4 (3) in 87% isolated yield. In situ NMR spectroscopy indicates that the reactions proceed through the insertion of the C�O bond in CO 2 into the Pd−H bond in 1b to form 2b, which sequentially reacts with the hydrides in NH 3 •BH 3 or NaBH 4 to produce boron formato species and regenerate 1b. This work represents one of the rare examples of catalytic transfer hydrogenation of CO 2 with NH 3 •BH 3 to the formic acid level under very mild conditions without any additives and also the first example of 4 equiv of CO 2 uptake by NaBH 4 in a reaction.

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Hydrogenation of CO₂ by a Tripodal Palladium Pincer Complex

Biswas,

Lönnecke,

Kirillov

et al. 2024

ACS Catal.

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This study presents the hydrogenation of carbon dioxide to formate catalyzed by a palladium catalyst based on a tripodal pincer ligand. Our work demonstrates how this catalyst design facilitates the formation of more hydridic anionic trigonal bipyramidal Pd−H species, efficiently promoting hydride transfer to CO 2 . Through experimental and theoretical studies, we demonstrated that our catalyst operates via a hydrogen activation mechanism involving the heterolytic splitting of H 2 between the sterically demanding trigonal pyramidal palladium fragment and the loosely coordinated PCy 3 ligand. Beyond the fundamental interest in understanding the reactivity of these compounds, our study describes a practical catalyst for CO 2 hydrogenation, demonstrating high turnover numbers (TON = 3.5 × 10 3 ) under mild reaction conditions.

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Reactions and catalytic applications of a PNCNP pincer palladium hydride complex

Abstract: A palladium(II) hydride complex supported by a benzene-based PNCNP pincer ligand, [2,6-(tBu2PNH)2C6H3]PdH (1), has been synthesized via two different routes: the reaction of the corresponding chloride complex with LiAlH4 and...

Cited by 3 publications

References 83 publications

Synthesis and Characterization of Novel Pd@rGO−CuFe₂O₄ Magnetic Nanoparticles: A Recyclable Catalyst for C−C Coupling Reaction in Biomass‐Derived Organic Solvent

Synthesis and Characterization of Novel Pd@rGO−CuFe₂O₄ Magnetic Nanoparticles: A Recyclable Catalyst for C−C Coupling Reaction in Biomass‐Derived Organic Solvent

Evaluating the Catalytic Activities of PNCNP Pincer Group 10 Metal Hydride Complexes: Pd-Catalyzed Reduction of CO₂ to the Formic Acid Level with NH₃·BH₃ and NaBH₄ under Ambient Conditions

Hydrogenation of CO₂ by a Tripodal Palladium Pincer Complex

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Reactions and catalytic applications of a PNCNP pincer palladium hydride complex

Abstract: A palladium(II) hydride complex supported by a benzene-based PNCNP pincer ligand, [2,6-(tBu2PNH)2C6H3]PdH (1), has been synthesized via two different routes: the reaction of the corresponding chloride complex with LiAlH4 and...

Cited by 3 publications

References 83 publications

Synthesis and Characterization of Novel Pd@rGO−CuFe2O4 Magnetic Nanoparticles: A Recyclable Catalyst for C−C Coupling Reaction in Biomass‐Derived Organic Solvent

Synthesis and Characterization of Novel Pd@rGO−CuFe2O4 Magnetic Nanoparticles: A Recyclable Catalyst for C−C Coupling Reaction in Biomass‐Derived Organic Solvent

Evaluating the Catalytic Activities of PNCNP Pincer Group 10 Metal Hydride Complexes: Pd-Catalyzed Reduction of CO2 to the Formic Acid Level with NH3·BH3 and NaBH4 under Ambient Conditions

Hydrogenation of CO2 by a Tripodal Palladium Pincer Complex

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Synthesis and Characterization of Novel Pd@rGO−CuFe₂O₄ Magnetic Nanoparticles: A Recyclable Catalyst for C−C Coupling Reaction in Biomass‐Derived Organic Solvent

Synthesis and Characterization of Novel Pd@rGO−CuFe₂O₄ Magnetic Nanoparticles: A Recyclable Catalyst for C−C Coupling Reaction in Biomass‐Derived Organic Solvent

Evaluating the Catalytic Activities of PNCNP Pincer Group 10 Metal Hydride Complexes: Pd-Catalyzed Reduction of CO₂ to the Formic Acid Level with NH₃·BH₃ and NaBH₄ under Ambient Conditions

Hydrogenation of CO₂ by a Tripodal Palladium Pincer Complex