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RESEARCH PAPER · Israel Journal of Chemistry · 2019

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

Kevin H. Shaughnessy

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Development of Palladium Precatalysts that Efficiently Generate LPd(0) Active SpeciesOriginalAir-stable Pd(0) catalyst bearing dual phosphine ligands: a detailed evaluation of air stability and catalytic property in cross-coupling reactions6Reductive activation of Pd II -precatalysts via decarboxylation of pivalate in direct C–H arylation reactions5Using ketones as catalyst activators in palladium-catalyzed cross- coupling reactions0Enolizable Ketones as Activators of Palladium(II) Precatalysts in Amine Arylation Reactions21Suzuki‐Miyaura Cross‐Coupling of Amides using Well‐Defined, Air‐Stable [(PR3)2Pd(II)X2] Precatalysts15A Next‐Generation Air‐Stable Palladium(I) Dimer Enables Olefin Migration and Selective C−C Coupling in Air53A Next‐Generation Air‐Stable Palladium(I) Dimer Enables Olefin Migration and Selective C−C Coupling in Air12Differences in the Performance of Allyl Based Palladium Precatalysts for Suzuki‐Miyaura Reactions30Aryl Amination with Soluble Weak Base Enabled by a Water-Assisted Mechanism0Effect of Aryl Ligand Identity on Catalytic Performance of Trineopentylphosphine Arylpalladium Complexes in N-Arylation Reactions6Catalysis with Palladium(I) Dimers112Catalysis with Palladium(I) Dimers16Detection and Characterization of Mononuclear Pd(I) Complexes Supported by N2S2 and N4 Tetradentate Ligands31Aryl Amination Using Soluble Weak Base Enabled by a Water-Assisted Mechanism35N-substituted aminobiphenyl palladacycles stabilized by dialkylterphenyl phosphanes: Preparation and applications in C N cross-coupling reactions9Pd-Catalysed Suzuki–Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides50DMP DAB–Pd–MAH: A Versatile Pd(0) Source for Precatalyst Formation, Reaction Screening, and Preparative-Scale Synthesis43Isolation and Catalytic Reactivity of Mononuclear Palladium(I) Complexes0Isolation and Catalytic Reactivity of Mononuclear Palladium(I) Complexes0The influence of the phosphine ligand nature on palladium catalysts in the norbornadiene allylation with allyl formate7Effect of Precatalyst Oxidation State in C–N Cross-Couplings with 2-Phosphinoimidazole-Derived Bimetallic Pd(I) and Pd(II) Complexes13Saturated Boronic Acids, Boronates, and Trifluoroborates: An Update on Their Synthetic and Medicinal Chemistry82Halogen‐Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions39Halogen‐verbrückte Methylnaphthylpalladium‐Dimere als vielseitig einsetzbare Katalysatorvorstufen in Kreuzkupplungen4An Alkoxy Modified N ‐Heterocyclic Carbene‐Palladacycle: Synthesis, Characterization and Application towards Buchwald‐Hartwig and Suzuki‐Miyaura Coupling Reactions7An air-stable, well-defined palladium–BIAN–NHC chloro dimer: a fast-activating, highly efficient catalyst for cross-coupling22Cyrene™ blends: a greener solvent system for organic syntheses31Formation of exceptional monomeric YPhos–PdCl 2 complexes with high activities in coupling reactions13LPdCl 2 (amine) complexes supported by terphenyl phosphanes: applications in aryl amination reactions5Aerobic Allylic Amination Catalyzed by a Pd(OAc)2/P(OPh)3 System with Low Catalyst Loading10Ylide-Substituted Phosphines: A Platform of Strong Donor Ligands for Gold Catalysis and Palladium-Catalyzed Coupling Reactions75Isolation and Catalytic Reactivity of Mononuclear Palladium(I) Complexes1Tunable Unsymmetrical Ferrocene Ligands Bearing a Bulky Di-1-adamantylphosphino Motif for Many Kinds of Csp2–Csp3 Couplings27Palladium complexes of PNNP type diiminodiphosphine ligands for the Suzuki C C coupling reactions7A Versatile Palladium Synthon: [Pd(NHC)(PhC≡CPh)]**16Well-Defined Pdn Clusters for Cross-Coupling and Hydrogenation Catalysis: New Opportunities for Catalyst Design47Emerging Trends in Cross-Coupling: Twelve-Electron-Based L 1 Pd(0) Catalysts, Their Mechanism of Action, and Selected Applications179Isolation and Characterization of Heteroleptic Mononuclear Palladium(I) Complexes32High-Throughput Synthetic Chemistry in Academia: Case Studies in Overcoming Barriers through Industrial Collaborations and Accessible Tools3Amines as Activating Ligands for Phosphine Palladium(II) Precatalysts: Effect of Amine Ligand Identity on the Catalyst Efficiency16Sustainable and practical formation of carbon–carbon and carbon–heteroatom bonds employing organo-alkali metal reagents20Boosting the activity of Mizoroki–Heck cross-coupling reactions with a supramolecular palladium catalyst favouring remote Zn⋯pyridine interactions5Übergangsmetallkatalysierte Kupplungsreaktionen0Visible light-induced palladium–carbon bond weakening in catalytically relevant T-shaped complexes21Expanding the Role of Dimeric Species: On-Cycle Involvement, Improved Stability, and Control of Stereo-Specificity. A Case Study of Atom-Economic Catalytic Hydrothiolation6Important Role of NH-Carbazole in Aryl Amination Reactions Catalyzed by 2-Aminobiphenyl Palladacycles17Convenient One-Pot Synthesis of L2Pd(0) Complexes for Cross-Coupling Catalysis9Active, selective, and stable single-component precatalysts for asymmetric allylic alkylation1Machine Learning-Guided Development of Trialkylphosphine Ni (I) Dimers and Applications in Site-Selective Catalysis43Suzuki–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 Precatalysts14We Already Know Everything about Oxidative Addition to Pd(0): Do We?50Palladates of the [NHC⋅H][Pd(NH 2 )(CC)Cl 2 ] Type as Effective Pre‐catalysts for the Formation of C−C and C−N Bonds9A tale of two metals: The Mizoroki-Heck reaction as a guide to compare the chemical characters of nickel and palladium in catalysis2Developing Ni and Pd precatalysts for demanding cross-coupling reactions0Synthesis and catalytic properties of palladium( ii ) complexes with P,π-chelating ferrocene phosphinoallyl ligands and their non-tethered analogues5Highly Ordered Mesoporous Polymer‐Supported Phosphine as the Ligand for Organometallic Reaction: Suzuki‐Miyaura Cross‐Coupling of Aryl Chlorides at Room Temperature4Palladium-Catalyzed Aminations in Flow ... on Water16Effects of Ring Size and Steric Encumbrance on Boron-to-Palladium Transmetalation from Arylboronic Esters6Radicalizing CO by Mononuclear Palladium(I)24Radikalisierung von CO durch einkerniges Palladium(I)1Alkene-Coordinated Palladium(0) Cross-Coupling Precatalysts: Comparing Oxidative Addition and Catalytic Reactivity for Dimethyl Fumarate and Maleic Anhydride Stabilizing Ligands7A Thermally Stable, Alkene-Free Palladium Source for Oxidative Addition Complex Formation and High-Turnover Catalysis12Palladium (II) Precursors for Clean In Situ Formation of Ad Hoc Cross‐Coupling Catalysts. Their Application in One‐Pot/Two‐Step Catalyses with 2‐Biaryl‐Dialkylphosphine Ligands6P,N‐Coordinating Ylide‐Functionalized Phosphines (NYPhos): A Ligand Platform for the Selective Monoarylation of Small Nucleophiles10P,N‐koordinierende Ylid‐funktionalisierte Phosphane (NYPhos): Eine Ligandenplattform für die selektive Monoarylierung kleiner Nukleophile1Palladium-Catalyzed Cross-Coupling Reaction via C–H Activation of Furanyl and Thiofuranyl Substrates5[(NHC)Pd(OAc)2]: Highly Active Carboxylate Pd(II)–NHC (NHC = N-Heterocyclic Carbene) Precatalysts for Suzuki–Miyaura and Buchwald–Hartwig Cross-Coupling of Amides by N–C(O) Activation14Pd-Methylnaphthyl-tBuBrettPhos Complexes as Efficient and Selective Catalysts for the Monoarylation of Ammonia and Hydrazine10C H activation of furanyl and thiofuranyl substrates catalyzed by trans-dichloro[1-cinnamyl-3-arylmethyl-benzimidazol-2-yliden]pyridine palladium(II) complexes8Halide Salts Alleviate TMSOK Inhibition in Suzuki–Miyaura Cross-Couplings7Pd‐Catalyzed Allylic Substitution Using Nucleophilic Amines: Access to Functionalized Mono‐ and Bis‐N‐Allyl Synthons2Experimental Evidence for Zerovalent Pd(NHC) as a Competent Catalyst in C–N Cross-Coupling (NHC = DiMeIHeptCl)19[Pd(NHC)(μ-Cl)Cl]2: The Highly Reactive Air- and Moisture-Stable, Well-Defined Pd(II)-N-Heterocyclic Carbene (NHC) Complexes for Cross-Coupling Reactions24Impact of the N-Heterocyclic Carbene (NHC) Ligand on the trans-[Pd(NHC)(NH2nBu)Cl2] Precatalyst Architecture in C–N Bond-Forming Reactions4Expedited Aminoglutarimide C–N Cross-Coupling Enabled by High-Throughput Experimentation6Tetranuclear N-Heterocyclic Carbene Palladium Acetate—The Fast-Initiating Precatalyst of Suzuki Coupling3A Half Century of the Sonogashira Reaction1Ligand Substitution, Catalyst Activation, and Oxidative Addition Studies of a Stable Dialkyl Palladium Precatalyst8C2-Selective Palladium-Catalyzed C–S Cross-Coupling of 2,4-Dihalopyrimidines10Catalyst Activation and Speciation Involving DyadPalladate Precatalysts in Suzuki–Miyaura and Buchwald–Hartwig Cross-Couplings6On-Demand Access to Palladium Oxidative Addition Complexes (OACs) from a Stable Organopalladate Salt10Aryl halide cross-coupling via formate-mediated transfer hydrogenation12Recent Green and Sustainable Pd‐Catalyzed Aminations12Access to Polysubstituted Pyrimidin-2-ones by Pd-Catalyzed [2 + 2 + 2] Cycloaddition of Alkyne-Tethered Malononitriles and Isocyanates6Shedding Light on the Precatalytic Mixture of Pd(OAc) 2 and Cooperating Bipyridone Ligands for the C─H Functionalization of Arenes2Oxidative Addition of Aryl Bromides at Palladium(I) to form Palladium(III) Complexes3Oxidative Addition of Aryl Bromides at Palladium(I) to form Palladium(III) Complexes1Dynamics of Metal–Metal Bond Dissociation in Pd–Pd and Ni–Ni Complexes: Reorganization and Redistribution Reactions of the Metalloradicals6Dynamics of Metal–Metal Bond Dissociation in Pd–Pd and Ni–Ni Complexes: Reorganization and Redistribution Reactions of the Metalloradicals1Aldehydes as CO Releasing Molecules: In Situ and Ex Situ Giese Reactions and Palladium-Catalyzed Aminocarbonylations4Palladium-Catalyzed Tsuji–Trost-Type Reactions in Bioorthogonal Chemistry: From Test Tubes to Living Systems3Hydrogen-Mediated Reductive Cross-Coupling of Aryl Iodides with Activated Aryl and Heteroaryl Bromides9Initiation of Palladium Precatalysts: Efficiency and Product Selectivity as a Function of Ligand, Substrate, and Reaction Conditions4A benzoxazolyl-linked cyclic(alkyl)(amino)carbene (CAAC): the N-sidearm negatively influences the Buchwald–Hartwig coupling2Balancing stability and reactivity: a robust Pd( ii ) biaryl precatalyst for rapid generation of catalytically active Pd(0) species0Transition Metal-Catalyzed Coupling Reactions1Palladium-catalysed synthesis of small-molecule epigenetic inhibitors as anticancer therapeutics0Synthesis, characterisation, crystal structure of silver and palladium N-heterocyclic carbene complexes, and investigation of their antimicrobial and catalytic activities1Selectivity for Exhaustive Cross-Coupling of Dihaloarenes Is Affected by the Interplay between the Halide Byproduct, Solvent, and Ligand1DNA-and BSA-binding properties of dichloro(1-methallyl-3-arylmethyl-5,6-dimethylbenzimidazolin-2-ylidene)pyridine palladium(II) complexes0Palladium(II) complexes with pyrimidine NHC (C*^Npyr) ligands in the Suzuki-Miyaura cross coupling reaction0Understanding Catalyst Activation Drives Transition from Iridium to Manganese Catalyzed Hydrogen Autotransfer Chemistry2Mild N‑Arylation of Sulfoximines With (Hetero)aryl Chlorides Enabled by α‐Methylnaphthyl‐ t BuBrettPhos Palladium Triflate3Unlocking Catalyst Activation as a Critical Bottleneck in Cross‐Coupling Reactions: Room‐Temperature Couplings of Weak Nucleophiles Enabled by [Pd(1‐MeNAP)TFA] 2 Precatalysts4Katalysatoraktivierung als Schlüsselfaktor in Kreuzkupplungen: Raumtemperatur‐Kupplungen schwacher Nukleophile ermöglicht durch [Pd(1‐MeNAP)TFA] 2 Präkatalysatoren0Comparative efficiency of palladium 2-aminobiphenyl RuPhos precatalysts of different generations in morpholine N-arylation with 1-chloro-4-fluorobenzene: kinetic and computational study0Metal-Catalyzed Reductive Coupling of Aryl Halides beyond Premetalated Reagents or Metallic Reductants: Biaryl Formation3Sustainable media for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions: current perspectives0Design and application of palladium(II)–acyl complexes as precatalysts for amination of aryl chlorides0Decoding the Selective Formation of One over Eight Possible Products in a Pd-Catalyzed Multicomponent Reaction0Two‐Coordinate 13‐Electron Pd I Complexes Stabilized by the Bulky DIMeIHept Cl NHC Ligand0

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  3. Using ketones as catalyst activators in palladium-catalyzed cross- coupling reactions

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  4. Enolizable Ketones as Activators of Palladium(II) Precatalysts in Amine Arylation Reactions

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  46. Important Role of NH-Carbazole in Aryl Amination Reactions Catalyzed by 2-Aminobiphenyl Palladacycles

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    Shiyi Yang, Xiang Yu, Yaxu Liu, Michele Tomasini, Lucia Caporaso, Albert Poater, Luigi Cavallo, Catherine S. J. Cazin, Steven P. Nolan, Michal Szostak

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