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RESEARCH PAPER · Organometallics · 2017

Mechanism of the Suzuki–Miyaura Cross-Coupling Reaction Mediated by [Pd(NHC)(allyl)Cl] Precatalysts

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Mechanism of the Suzuki–Miyaura Cross-Coupling Reaction Mediated by [Pd(NHC)(allyl)Cl] PrecatalystsOriginalSuzuki–Miyaura cross-coupling of amides and esters at room temperature: correlation with barriers to rotation around C–N and C–O bonds160Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water32Cyclopalladation in the Periphery of a NHC Ligand as the Crucial Step in the Synthesis of Highly Active Suzuki–Miyaura Cross‐Coupling Catalysts24Aqueous-Phase Chemistry of η3-Allylpalladium(II) Complexes with Sulfonated N -Heterocyclic Carbene Ligands: Solvent Effects in the Protolysis of Pd–C Bonds and Suzuki–Miyaura Reactions17The role of the metal in the dual-metal catalysed hydrophenoxylation of diphenylacetylene15Pd‐PEPPSI: Water‐Assisted Suzuki−Miyaura Cross‐Coupling of Aryl Esters at Room Temperature using a Practical Palladium‐NHC (NHC=N‐Heterocyclic Carbene) Precatalyst57Designing Pd and Ni Catalysts for Cross-Coupling Reactions by Minimizing Off-Cycle Species98Mechanistic Study of Suzuki–Miyaura Cross‐Coupling Reactions of Amides Mediated by [Pd(NHC)(allyl)Cl] Precatalysts99Monitoring of the Phosphine Role in the Mechanism of Palladium-Catalyzed Benzosilole Formation from Aryloxyethynyl Silanes20Structure and Reactivity of Pd Complexes in Various Oxidation States in Identical Ligand Environments with Reference to C–C and C–Cl Coupling Reactions: Insights from Density Functional Theory23Pd immobilized on dendrimer decorated halloysite clay: Computational and experimental study on the effect of dendrimer generation, Pd valance and incorporation of terminal functionality on the catalytic activity80Sterically hindered N-aryl/benzyl substituted piperidoimidazolin-2-ylidene palladium complexes and their catalytic activities9Novel Magnetically-Recyclable, Nitrogen-Doped Fe3O4@Pd NPs for Suzuki–Miyaura Coupling and Their Application in the Synthesis of Crizotinib17Computational Approach to Molecular Catalysis by 3d Transition Metals: Challenges and Opportunities423In situ transformations of Pd/NHC complexes with N-heterocyclic carbene ligands of different nature into colloidal Pd nanoparticles26The role of palladium nanoparticles in catalytic C–C cross-coupling reactions209Discovery of Polyoxo-Noble-Metalate-Based Metal–Organic Frameworks59Mixed N-heterocycles/N-heterocyclic carbene palladium(II) allyl complexes as precatalysts for direct arylation of azoles with aryl bromides17Computational Study on the Mechanism and Origin of the Regioselectivity and Stereospecificity in Pd/SIPr-Catalyzed Ring-Opening Cross-Coupling of 2-Arylaziridines with Arylboronic Acids21[Pd(NHC)(acac)Cl]: Well-Defined, Air-Stable, and Readily Available Precatalysts for Suzuki and Buchwald–Hartwig Cross-coupling (Transamidation) of Amides and Esters by N–C/O–C Activation109Engineering Metal–Organic Framework Catalysts for C−C and C−X Coupling Reactions: Advances in Reticular Approaches from 2014–201837Development of Palladium Precatalysts that Efficiently Generate LPd(0) Active Species112Colloidal metal oxide nanocrystals in catalysis9Three-phenyl transfer in palladium-catalyzed C C coupling reactions by triarylbismuths: A mechanistic study5Allylation of β-amino phosphonic acid precursor via palladium-NHC catalyzed allylic C–H activation15DFT Study of Unstrained Ketone C-C Bond Activation via Rhodium(I)-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions1Buchwald–Hartwig cross-coupling of amides (transamidation) by selective N–C(O) cleavage mediated by air- and moisture-stable [Pd(NHC)(allyl)Cl] precatalysts: catalyst evaluation and mechanism76Suzuki‐Miyaura Cross‐Coupling of Amides using Well‐Defined, Air‐Stable [(PR3)2Pd(II)X2] Precatalysts15Long-Distance Chirality Transfer from P-Ligand to Prochiral Dihydrosilanes via Pd(II) Aryl Iodide Complex in Pd-Catalyzed Silylation of Aryl Iodide: A DFT Study28Group IV diamine bis(phenolate) catalysts for 1-decene oligomerization44Mechanism of the Facile Nitrous Oxide Fixation by Homogeneous Ruthenium Hydride Pincer Catalysts22N,N′‐bridged binuclear NHC palladium complexes: A combined experimental catalytic and computational study for the Suzuki reaction15Polyoxopalladate-Loaded Metal–Organic Framework (POP@MOF): Synthesis and Heterogeneous Catalysis39Aromatic Substitution3Toward prediction of the precatalyst activation mechanism through the cross‐coupling reactions: Reduction of Pd( II ) to Pd(0) in precatalyst of the type Pd‐PEPPSI18Mechanism in palladium-catalyzed dearomative allylic reactions of benzyl phosphates with allyl borates: Insights from DFT calculations2Comparative study of aryl halides in Pd-mediated reactions: key factors beyond the oxidative addition step47C(acyl)–C(sp 2 ) and C(sp 2 )–C(sp 2 ) Suzuki–Miyaura cross-coupling reactions using nitrile-functionalized NHC palladium complexes9Evidence for “cocktail”-type catalysis in Buchwald–Hartwig reaction. A mechanistic study30Suzuki–Miyaura cross-coupling of esters by selective O–C(O) cleavage mediated by air- and moisture-stable [Pd(NHC)(μ-Cl)Cl] 2 precatalysts: catalyst evaluation and mechanism61Aminomethylpyridinequinones as new ligands for PEPPSI-type complexes4Pd on nitrogen rich polymer–halloysite nanocomposite as an environmentally benign and sustainable catalyst for hydrogenation of polyalfaolefin based lubricants631‐Decene oligomerization by new complexes bearing diamine‐diphenolates ligands: Effect of ligand structure33Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes11Mechanistic Aspects of the Palladium‐Catalyzed Suzuki‐Miyaura Cross‐Coupling Reaction281The direct C(sp2)-H functionalization and coupling of aromatic N-heterocycles with (hetero)aryl bromides by [PdX2(imidazolidin-2-ylidene)(Py)] catalysts12Site-Selective Cross-Coupling of Polyhalogenated Arenes and Heteroarenes with Identical Halogen Groups137Unveiling the full reaction path of the Suzuki–Miyaura cross-coupling in a single-molecule junction101[Pd(4-RSi-IPr)(allyl)Cl]/KCO/EtOH: A highly effective catalytic system for the Suzuki-Miyaura cross-coupling reaction6Which Type of Pincer Complex Is Thermodynamically More Stable? Understanding the Structures and Relative Bond Strengths of Group 10 Metal Complexes Supported by Benzene-Based PYCYP Pincer Ligands13Ni( i )–TPA stabilization by hydrogen bond formation on the second coordination sphere: a DFT characterization4One-step synthesis of PdCu@Ti 3 C 2 with high catalytic activity in the Suzuki–Miyaura coupling reaction9Palladium-catalyzed Suzuki–Miyaura cross-coupling with α -aminophosphonates based on 1,3,4-oxadiazole as ligands9A comprehensive review on green perspectives of electrocoagulation integrated with advanced processes for effective pollutants removal from water environment144Linker Engineering of 2D Imine Covalent Organic Frameworks for the Heterogeneous Palladium-Catalyzed Suzuki Coupling Reaction32Hierarchical TiO2 microspheres supported ultrasmall palladium Nanocrystals: A highly efficient catalyst for Suzuki reaction5Buchwald–Hartwig Amination and C–S/S–H Metathesis of Aryl Sulfides by Selective C–S Cleavage Mediated by Air- and Moisture-Stable [Pd(NHC)(μ-Cl)Cl]2 Precatalysts: Unified Mechanism for Activation of Inert C–S Bonds26Pd-NHC catalysed regioselective activation of B(3,6)–H of o -carborane – a synergy between experiment and theory4A Non Expected Alternative Ni(0) Species in the Ni‐Catalytic Aldehyde and Alcohol Arylation Reactions Facilitated by a 1,5‐Diaza‐3,7‐diphosphacyclooctane Ligand5Transition metal-free synthesis of 2-aryl quinazolines via alcohol dehydrogenation16Suzuki–Miyaura Cross-Coupling of Amides by N–C Cleavage Mediated by Air-Stable, Well-Defined [Pd(NHC)(sulfide)Cl2] Catalysts: Reaction Development, Scope, and Mechanism11Heteroaryl–Heteroaryl Suzuki–Miyaura Cross-Coupling Enabled by Large-but-Flexible Dibenzobarrelene-Derived Pd-NHC Precatalysts14A new air-stable Pd-PEPPSI N-heterocyclic carbene complex: Synthesis, structure, computational and catalytical studies11% V Bur index and steric maps: from predictive catalysis to machine learning126Base‐Ionizable Anionic NHC Ligands in Pd‐catalyzed Reactions of Aryl Chlorides15Dibenzobarrelene-derived Pd-NHCs: efficient precatalysts for the Suzuki–Miyaura polycondensations of dichloroarene monomers4New conjugated carbazole derivatives: synthesis and photophysical properties catalysed by Pd–Cu@rGO4Suzuki–Miyaura cross-coupling reaction catalyzed by [R3Si–IPr]Pd complexes: a computational study2Tuning the steric hindrance of alkylamines: a predictive model of steric editing of planar amines15Pd–PEPPSI-type expanded ring N-heterocyclic carbene complexes: synthesis, characterization, and catalytic activity in Suzuki–Miyaura cross coupling5Design and Synthesis of a Novel Catalytic System Based on Pd Supported on Alumina Extrudates for Hydrotreating of PAO Lubricants4Functionalized Covalent Triazine Framework (CTF) for Catalytic CO2 Fixation and Synthesis of Value-Added Chemicals21Investigating Arylazoformamide Ligands in Palladium(II) Precatalysts through the Suzuki–Miyaura Cross-Coupling Reaction5The influential IPr: 25 years after its discovery27PEPPSI-type N-heterocyclic carbene palladium(II) complexes as catalysts in the direct C5 arylation of furan and thiophene2Palladium-NHC mediated telomerization of aromatic alcohols3A Well‐Defined Pd‐NHC Pre‐Catalyst for the Borylation of Aryl Chlorides4Structurally Flexible (Thiazol-2-ylidene)Pd(Allyl)Cl Complexes for Suzuki–Miyaura Cross-Coupling of Aryl Halides and Amides1DFT in catalysis: Complex equations for practical computing applications in chemistry13Analyzing the Solvent Effects in Palladium/ N -Heterocyclic Carbene (Pd/NHC)-Catalyzed Suzuki–Miyaura Coupling of Aryl Chlorides: A Computational Study of the Oxidative Addition Step with Experimental Validation0Mechanistic Insights into Nickel–NHC-Catalyzed Alkene Isomerization: A Computational Study on Selectivity and Reactivity1Well‐Defined Nickel Precatalysts: Form, Function, and Application0

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  1. Suzuki–Miyaura cross-coupling of amides and esters at room temperature: correlation with barriers to rotation around C–N and C–O bonds

    Chemical Science · 2017-01-01

    Peng Lei, Guangrong Meng, Shicheng Shi, Yun Ling, Jie An, Roman Szostak, Michal Szostak

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  2. Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water

    Dalton Transactions · 2017-01-01

    V. Ramakrishna, Nareddula Dastagiri Reddy

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  3. Cyclopalladation in the Periphery of a NHC Ligand as the Crucial Step in the Synthesis of Highly Active Suzuki–Miyaura Cross‐Coupling Catalysts

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    Agnes Fizia, Maximilian Gaffga, Johannes Lang, Yu Sun, Gereon Niedner‐Schatteburg, Werner Richard Thiel

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  4. Aqueous-Phase Chemistry of η3-Allylpalladium(II) Complexes with Sulfonated N -Heterocyclic Carbene Ligands: Solvent Effects in the Protolysis of Pd–C Bonds and Suzuki–Miyaura Reactions

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  5. The role of the metal in the dual-metal catalysed hydrophenoxylation of diphenylacetylene

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  6. Pd‐PEPPSI: Water‐Assisted Suzuki−Miyaura Cross‐Coupling of Aryl Esters at Room Temperature using a Practical Palladium‐NHC (NHC=N‐Heterocyclic Carbene) Precatalyst

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  7. Designing Pd and Ni Catalysts for Cross-Coupling Reactions by Minimizing Off-Cycle Species

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  8. Mechanistic Study of Suzuki–Miyaura Cross‐Coupling Reactions of Amides Mediated by [Pd(NHC)(allyl)Cl] Precatalysts

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  9. Monitoring of the Phosphine Role in the Mechanism of Palladium-Catalyzed Benzosilole Formation from Aryloxyethynyl Silanes

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  10. Structure and Reactivity of Pd Complexes in Various Oxidation States in Identical Ligand Environments with Reference to C–C and C–Cl Coupling Reactions: Insights from Density Functional Theory

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  11. Pd immobilized on dendrimer decorated halloysite clay: Computational and experimental study on the effect of dendrimer generation, Pd valance and incorporation of terminal functionality on the catalytic activity

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  12. Sterically hindered N-aryl/benzyl substituted piperidoimidazolin-2-ylidene palladium complexes and their catalytic activities

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  13. Novel Magnetically-Recyclable, Nitrogen-Doped Fe3O4@Pd NPs for Suzuki–Miyaura Coupling and Their Application in the Synthesis of Crizotinib

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  14. Computational Approach to Molecular Catalysis by 3d Transition Metals: Challenges and Opportunities

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  15. In situ transformations of Pd/NHC complexes with N-heterocyclic carbene ligands of different nature into colloidal Pd nanoparticles

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  16. The role of palladium nanoparticles in catalytic C–C cross-coupling reactions

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  17. Discovery of Polyoxo-Noble-Metalate-Based Metal–Organic Frameworks

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  18. Mixed N-heterocycles/N-heterocyclic carbene palladium(II) allyl complexes as precatalysts for direct arylation of azoles with aryl bromides

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  19. Computational Study on the Mechanism and Origin of the Regioselectivity and Stereospecificity in Pd/SIPr-Catalyzed Ring-Opening Cross-Coupling of 2-Arylaziridines with Arylboronic Acids

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  20. [Pd(NHC)(acac)Cl]: Well-Defined, Air-Stable, and Readily Available Precatalysts for Suzuki and Buchwald–Hartwig Cross-coupling (Transamidation) of Amides and Esters by N–C/O–C Activation

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  22. Development of Palladium Precatalysts that Efficiently Generate LPd(0) Active Species

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  23. Colloidal metal oxide nanocrystals in catalysis

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  24. Three-phenyl transfer in palladium-catalyzed C C coupling reactions by triarylbismuths: A mechanistic study

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  26. DFT Study of Unstrained Ketone C-C Bond Activation via Rhodium(I)-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions

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  27. Buchwald–Hartwig cross-coupling of amides (transamidation) by selective N–C(O) cleavage mediated by air- and moisture-stable [Pd(NHC)(allyl)Cl] precatalysts: catalyst evaluation and mechanism

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  29. Long-Distance Chirality Transfer from P-Ligand to Prochiral Dihydrosilanes via Pd(II) Aryl Iodide Complex in Pd-Catalyzed Silylation of Aryl Iodide: A DFT Study

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  30. Group IV diamine bis(phenolate) catalysts for 1-decene oligomerization

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  31. Mechanism of the Facile Nitrous Oxide Fixation by Homogeneous Ruthenium Hydride Pincer Catalysts

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  32. N,N′‐bridged binuclear NHC palladium complexes: A combined experimental catalytic and computational study for the Suzuki reaction

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  33. Polyoxopalladate-Loaded Metal–Organic Framework (POP@MOF): Synthesis and Heterogeneous Catalysis

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  34. Aromatic Substitution

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  35. Toward prediction of the precatalyst activation mechanism through the cross‐coupling reactions: Reduction of Pd( II ) to Pd(0) in precatalyst of the type Pd‐PEPPSI

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  36. Mechanism in palladium-catalyzed dearomative allylic reactions of benzyl phosphates with allyl borates: Insights from DFT calculations

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  37. Comparative study of aryl halides in Pd-mediated reactions: key factors beyond the oxidative addition step

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  38. C(acyl)–C(sp 2 ) and C(sp 2 )–C(sp 2 ) Suzuki–Miyaura cross-coupling reactions using nitrile-functionalized NHC palladium complexes

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  39. Evidence for “cocktail”-type catalysis in Buchwald–Hartwig reaction. A mechanistic study

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  40. Suzuki–Miyaura cross-coupling of esters by selective O–C(O) cleavage mediated by air- and moisture-stable [Pd(NHC)(μ-Cl)Cl] 2 precatalysts: catalyst evaluation and mechanism

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  41. Aminomethylpyridinequinones as new ligands for PEPPSI-type complexes

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  42. Pd on nitrogen rich polymer–halloysite nanocomposite as an environmentally benign and sustainable catalyst for hydrogenation of polyalfaolefin based lubricants

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  43. 1‐Decene oligomerization by new complexes bearing diamine‐diphenolates ligands: Effect of ligand structure

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  44. Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes

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  45. Mechanistic Aspects of the Palladium‐Catalyzed Suzuki‐Miyaura Cross‐Coupling Reaction

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  46. The direct C(sp2)-H functionalization and coupling of aromatic N-heterocycles with (hetero)aryl bromides by [PdX2(imidazolidin-2-ylidene)(Py)] catalysts

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  47. Site-Selective Cross-Coupling of Polyhalogenated Arenes and Heteroarenes with Identical Halogen Groups

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  48. Unveiling the full reaction path of the Suzuki–Miyaura cross-coupling in a single-molecule junction

    Nature Nanotechnology · 2021-09-02

    Chen Yang, Lei Zhang, Chenxi Lu, Shuyao Zhou, Xingxing Li, Yanwei Li, Yang Yang, Yu Li, Zhirong Liu, Jinlong Yang, Kendall N. Houk, Fanyang Mo, Xuefeng Guo

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  49. [Pd(4-RSi-IPr)(allyl)Cl]/KCO/EtOH: A highly effective catalytic system for the Suzuki-Miyaura cross-coupling reaction

    Journal of Organometallic Chemistry · 2021-09-24

    Yuto Seo, Wahyu S. Putro, Miftah Faried, Vladimir Ya. Lee, Tomoteru Mizusaki, Yukio Takagi, Yoong‐Kee Choe, Kazuhiro Matsumoto, Jun‐Chul Choi, Norihisa Fukaya

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  50. Which Type of Pincer Complex Is Thermodynamically More Stable? Understanding the Structures and Relative Bond Strengths of Group 10 Metal Complexes Supported by Benzene-Based PYCYP Pincer Ligands

    Inorganic Chemistry · 2021-12-08

    Fei Fang, Jiaxin Kang, Cong‐Qiao Xu, Jiarui Chang, Jie Zhang, Shujun Li, Xuenian Chen

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