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Lewis Acid Acceleration of C−N Bond-Forming Reductive Elimination from Heteroarylpalladium Complexes and Catalytic Amidation of Heteroaryl Bromides

https://doi.org/10.1021/ja0722473
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What this work says

Outgoing claims: the papers this work cites, builds on, or argues with.

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Palladium-Catalyzed Amination of Aryl Halides and Related Reactions
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Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates
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Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates
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Highly Reactive, General, and Long‐Lived Catalysts for Coupling Heteroaryl and Aryl Chlorides with Primary Nitrogen Nucleophiles
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Monodentate Phosphines Provide Highly Active Catalysts for Pd‐Catalyzed CN Bond‐Forming Reactions of Heteroaromatic Halides/Amines and (H)N‐Heterocycles
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Kernresonanzspektroskopische Untersuchungen an Borverbindungen, VII. 11B‐ und 14N‐ Kernresonanzstudien an tetrakoordinierten Bor‐Stickstoff‐Verbindungen
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Heteroaromatic Thioether—Boronic Acid Cross‐Coupling under Neutral Reaction Conditions.
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Pd‐Catalyzed N‐Arylation of Heteroarylamines.
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Practical Palladium Catalysts for C-N and C-O Bond Formation
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Palladium-catalyzed amination of aryl halides and sulfonates
inferredcites →https://doi.org/10.1021/ar970282gopenalex-snapshot
Carbon−Heteroatom Bond-Forming Reductive Eliminations of Amines, Ethers, and Sulfides
inferredcites →https://doi.org/10.1021/ic951131hopenalex-snapshot
Rhodium and Palladium Complexes of a 3,5-Lutidine-Based Phosphine Ligand
inferredcites →https://doi.org/10.1021/ic960285+openalex-snapshot
Formation and X-ray Structures of PCP Ligand Based Platinum(II) and Palladium(II) Macrocycles
inferredcites →https://doi.org/10.1021/ja012610kopenalex-snapshot
Pd-Catalyzed Intermolecular Amidation of Aryl Halides: The Discovery that Xantphos Can Be Trans-Chelating in a Palladium Complex
inferredcites →https://doi.org/10.1021/ja0260465openalex-snapshot
A General and Efficient Copper Catalyst for the Amidation of Aryl Halides
inferredcites →https://doi.org/10.1021/ja0315107openalex-snapshot
Synthesis, Structure, and Reductive Elimination Chemistry of Three-Coordinate Arylpalladium Amido Complexes
inferredcites →https://doi.org/10.1021/ja056076iopenalex-snapshot
Palladium-Catalyzed Intermolecular α-Arylation of Zinc Amide Enolates under Mild Conditions
inferredcites →https://doi.org/10.1021/ja971057xopenalex-snapshot
Carbon−Nitrogen-Bond-Forming Reductive Elimination of Arylamines from Palladium(II) Phosphine Complexes
inferredcites →https://doi.org/10.1021/jo026510oopenalex-snapshot
Lewis Acid-Promoted Oxidative Addition of Thioimidates to Pd(0)
inferredcites →https://doi.org/10.1021/ol005654ropenalex-snapshot
Palladium-Catalyzed Intermolecular Coupling of Aryl Halides and Amides
inferredcites →https://doi.org/10.1021/ol0200091openalex-snapshot
Heteroaromatic Thioether−Boronic Acid Cross-Coupling under Neutral Reaction Conditions
inferredcites →https://doi.org/10.1021/ol0265923openalex-snapshot
Pd-catalyzed N-arylation of heteroarylamines.
inferredcites →https://doi.org/10.1021/ol035655uopenalex-snapshot
Palladium-Catalyzed Intermolecular Coupling of Aryl Chlorides and Sulfonamides under Microwave Irradiation
inferredcites →https://doi.org/10.1021/ol0357696openalex-snapshot
Selective Amination of Polyhalopyridines Catalyzed by a Palladium−Xantphos Complex
inferredcites →https://doi.org/10.1021/ol049091lopenalex-snapshot
Novel N-Aryl and N-Heteroaryl Sulfamide Synthesis via Palladium Cross Coupling
inferredcites →https://doi.org/10.1021/om00079a008openalex-snapshot
Catalytic hydrocyanation of olefins by nickel(0) phosphite complexes - effects of Lewis acids
inferredcites →https://doi.org/10.1021/om030257gopenalex-snapshot
Understanding the Coupling of Heteroaromatic Substrates: Synthesis, Structures, and Reductive Eliminations of Heteroarylpalladium Amido Complexes
inferredcites →https://doi.org/10.1021/om980897xopenalex-snapshot
Lewis Acids Accelerate Reductive Elimination of RCN from P2Pd(R)(CN)

What points at this work

Incoming claims: where this work appears in other papers’ reference lists and arguments.

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Palladium N(CH2CH2PiPr2)2-Dialkylamides: Synthesis, Structural Characterization, and Reactivity
inferred← citeshttps://doi.org/10.1021/ja075041aopenalex-snapshot
Oxidative Diamination of Alkenes with Ureas as Nitrogen Sources: Mechanistic Pathways in the Presence of a High Oxidation State Palladium Catalyst
inferred← citeshttps://doi.org/10.1021/ja106514bopenalex-snapshot
Selective C-4 Alkylation of Pyridine by Nickel/Lewis Acid Catalysis
inferred← citeshttps://doi.org/10.1021/ja301375copenalex-snapshot
Intramolecular Oxycyanation of Alkenes by Cooperative Pd/BPh3 Catalysis
inferred← citeshttps://doi.org/10.1021/ja306178qopenalex-snapshot
Lewis Acid-Triggered Selective Zincation of Chromones, Quinolones, and Thiochromones: Application to the Preparation of Natural Flavones and Isoflavones
inferred← citeshttps://doi.org/10.1021/ja4068172openalex-snapshot
Nickel-Catalyzed Decarbonylative Alkylidenation of Phthalimides with Trimethylsilyl-Substituted Alkynes
inferred← citeshttps://doi.org/10.1021/ja4122632openalex-snapshot
Intramolecular Aminocyanation of Alkenes by Cooperative Palladium/Boron Catalysis
inferred← citeshttps://doi.org/10.1021/ja5008596openalex-snapshot
1,2-Selective Hydrosilylation of Conjugated Dienes
inferred← citeshttps://doi.org/10.1021/ja710766jopenalex-snapshot
A Strategy for C−H Activation of Pyridines: Direct C-2 Selective Alkenylation of Pyridines by Nickel/Lewis Acid Catalysis
inferred← citeshttps://doi.org/10.1021/ja9044357openalex-snapshot
Pd-Catalyzed N-Arylation of Secondary Acyclic Amides: Catalyst Development, Scope, and Computational Study
inferred← citeshttps://doi.org/10.1021/jacs.0c06370openalex-snapshot
A Synthetic Approach to Dimetalated Arenes Using Flow Microreactors and the Switchable Application to Chemoselective Cross-Coupling Reactions
inferred← citeshttps://doi.org/10.1021/jacs.1c06419openalex-snapshot
Heteroaryl–Heteroaryl, Suzuki–Miyaura, Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate
inferred← citeshttps://doi.org/10.1021/jacs.5c06124openalex-snapshot
Metal Electronics Mediate Steric and Coordination Number Effects on Palladium(II) C–X Reductive Elimination
inferred← citeshttps://doi.org/10.1021/jacs.7b00049openalex-snapshot
Decarbonylative Diaryl Ether Synthesis by Pd and Ni Catalysis
inferred← citeshttps://doi.org/10.1021/jacs.7b09488openalex-snapshot
Cross-Coupling of Primary Amides to Aryl and Heteroaryl Partners Using (DiMeIHeptCl)Pd Promoted by Trialkylboranes or B(C6F5)3
inferred← citeshttps://doi.org/10.1021/jacs.9b03291openalex-snapshot
Palladium-Catalyzed α-Arylation of Carboxylic Acids and Secondary Amides via a Traceless Protecting Strategy
inferred← citeshttps://doi.org/10.1021/jo200443uopenalex-snapshot
A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates
inferred← citeshttps://doi.org/10.1021/jo3005827openalex-snapshot
Palladium-Catalyzed Amidation of Aryl Halides Using 2-Dialkylphosphino-2′-alkoxyl-1,1′-binaphthyl as Ligands
inferred← citeshttps://doi.org/10.1021/jo301121fopenalex-snapshot
Evolution of a Protecting-Group-Free Total Synthesis: Studies en Route to the Neuroactive Marine Macrolide (−)-Palmyrolide A
inferred← citeshttps://doi.org/10.1021/jo4024792openalex-snapshot
Syntheses of Fused Tetracyclic Quinolines via Ugi-Variant MCR and Pd-Catalyzed Bis-annulation
inferred← citeshttps://doi.org/10.1021/jo402618ropenalex-snapshot
Synthesis of Trimethylstannyl Arylboronate Compounds by Sandmeyer-Type Transformations and Their Applications in Chemoselective Cross-Coupling Reactions
inferred← citeshttps://doi.org/10.1021/jo502274topenalex-snapshot
Palladium-Catalyzed peri-Selective Chalcogenation of Naphthylamines with Diaryl Disulfides and Diselenides via C–H Bond Cleavage
inferred← citeshttps://doi.org/10.1021/ol100263ropenalex-snapshot
Copper-Mediated N -Heteroarylation of Primary Sulfonamides: Synthesis of Mono- N -heteroaryl Sulfonamides
inferred← citeshttps://doi.org/10.1021/ol100720xopenalex-snapshot
Pd-Catalyzed Cross-Coupling Reactions of Amides and Aryl Mesylates
inferred← citeshttps://doi.org/10.1021/ol2000827openalex-snapshot
Synthesis of α-Carbolines via Pd-Catalyzed Amidation and Vilsmeier−Haack Reaction of 3-Acetyl-2-chloroindoles
inferred← citeshttps://doi.org/10.1021/ol300570fopenalex-snapshot
The Regioselective Switch for Amino-NHC Mediated C–H Activation of Benzimidazole via Ni–Al Synergistic Catalysis
inferred← citeshttps://doi.org/10.1021/ol301606yopenalex-snapshot
Ni-Catalyzed Alkenylation of Triazolopyridines: Synthesis of 2,6-Disubstituted Pyridines
inferred← citeshttps://doi.org/10.1021/ol302571topenalex-snapshot
Chemoselective Cross-Coupling Reactions with Differentiation between Two Nucleophilic Sites on a Single Aromatic Substrate
inferred← citeshttps://doi.org/10.1021/ol4007162openalex-snapshot
One-Pot Synthesis of Diarylamines from Two Aromatic Amines via Oxidative Dearomatization–Imino Exchange–Reductive Aromatization
inferred← citeshttps://doi.org/10.1021/ol401923jopenalex-snapshot
Dual Selectivity: Electrophile and Nucleophile Selective Cross-Coupling Reactions on a Single Aromatic Substrate
inferred← citeshttps://doi.org/10.1021/ol4035947openalex-snapshot
Palladium-Catalyzed Amination of Unprotected Five-Membered Heterocyclic Bromides
inferred← citeshttps://doi.org/10.1021/ol801285gopenalex-snapshot
Water-Mediated Catalyst Preactivation: An Efficient Protocol for C−N Cross-Coupling Reactions
inferred← citeshttps://doi.org/10.1021/ol801332nopenalex-snapshot
α-Pyridylation of Chiral Amines via Urea Coupling, Lithiation and Rearrangement
inferred← citeshttps://doi.org/10.1021/ol801784aopenalex-snapshot
Efficient Iron-Catalyzed N-Arylation of Aryl Halides with Amines
inferred← citeshttps://doi.org/10.1021/om100996eopenalex-snapshot
Theoretical Study on Mechanism of Copper(I)-Catalyzed Cross-Coupling between Aryl Halides and Alkylamines
inferred← citeshttps://doi.org/10.1021/om500682sopenalex-snapshot
Synthesis and Reactivity of a Nucleophilic Palladium(II) Carbene
inferred← citeshttps://doi.org/10.1021/om8008298openalex-snapshot
Bi- and Trinuclear Complexes of Group 4 Metal and Palladium Bridged by OPPh2Groups: Synthesis and High Catalytic Activities in Double Hydrophosphinylation of 1-Octyne
inferred← citeshttps://doi.org/10.1038/nchem.2900openalex-snapshot
Iridium-catalysed arylation of C–H bonds enabled by oxidatively induced reductive elimination
inferred← citeshttps://doi.org/10.1038/s41467-026-68302-wopenalex-snapshot
Lewis acid-triggered hydroxyl spillover enables selective urea electrooxidation to nitrite with concurrent energy-saving hydrogen production
inferred← citeshttps://doi.org/10.1038/srep12005openalex-snapshot
Visible-light-driven Photocatalytic N-arylation of Imidazole Derivatives and Arylboronic Acids on Cu/graphene catalyst
inferred← citeshttps://doi.org/10.1039/b806211kopenalex-snapshot
Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions
inferred← citeshttps://doi.org/10.1039/b819162jopenalex-snapshot
Nickel-catalysed denitrogenative alkyne insertion reactions of N-sulfonyl-1,2,3-triazoles
inferred← citeshttps://doi.org/10.1039/b823407hopenalex-snapshot
Copper catalyzed coupling of aryl chlorides, bromides and iodides with amines and amides
inferred← citeshttps://doi.org/10.1039/b904127copenalex-snapshot
A new route to 3-acyl-2-aminobenzofurans: palladium-catalysed cycloisomerisation of 2-(cyanomethyl)phenyl esters
inferred← citeshttps://doi.org/10.1039/b909803hopenalex-snapshot
Manganese-catalyzed cross-coupling reactions of nitrogen nucleophiles with aryl halides in water
inferred← citeshttps://doi.org/10.1039/b917010copenalex-snapshot
Ligand-free iron/copper cocatalyzed N-arylations of aryl halides with amines under microwave irradiation
inferred← citeshttps://doi.org/10.1039/c0sc00330aopenalex-snapshot
Palladium-catalyzed coupling of functionalized primary and secondary amines with aryl and heteroaryl halides: two ligands suffice in most cases
inferred← citeshttps://doi.org/10.1039/c2ob26516hopenalex-snapshot
Divergent synthesis of novel 9-deazaxanthine derivatives via late-stage cross-coupling reactions
inferred← citeshttps://doi.org/10.1039/c2sc21673fopenalex-snapshot
Additive effects on palladium-catalyzed deprotonative-cross-coupling processes (DCCP) of sp 3 C–H bonds in diarylmethanes
inferred← citeshttps://doi.org/10.1039/c3nj01355copenalex-snapshot
Cycloalkenyl nonaflates as electrophilic cross-coupling substrates for palladium catalyzed C–N bond forming reactions with enolizable heterocycles under microwave enhanced conditions
inferred← citeshttps://doi.org/10.1039/c3ra46548aopenalex-snapshot
Nano copper(i) oxide/zinc oxide catalyzed N-arylation of nitrogen-containing heterocycles with aryl halides and arylboronic acids in air
inferred← citeshttps://doi.org/10.1039/c3sc53414fopenalex-snapshot
Non-directed allylic C–H acetoxylation in the presence of Lewis basic heterocycles
inferred← citeshttps://doi.org/10.1039/c4ob00846dopenalex-snapshot
A general catalyst for Suzuki–Miyaura and Sonogashira reactions of aryl and heteroaryl chlorides in water
inferred← citeshttps://doi.org/10.1039/c4ob02436bopenalex-snapshot
Efficient phosphine ligands for the one-pot palladium-catalyzed borylation/Suzuki–Miyaura cross-coupling reaction
inferred← citeshttps://doi.org/10.1039/c4ra06804aopenalex-snapshot
Nanoparticle mediated organic synthesis (NAMO-synthesis): CuI-NP catalyzed ligand free amidation of aryl halides
inferred← citeshttps://doi.org/10.1039/c5ob01934fopenalex-snapshot
Pd-indenyl-diphosphine: an effective catalyst for the preparation of triarylamines
inferred← citeshttps://doi.org/10.1039/c5sc02739jopenalex-snapshot
Chemoselective palladium-catalyzed deprotonative arylation/[1,2]-Wittig rearrangement of pyridylmethyl ethers
inferred← citeshttps://doi.org/10.1039/c6cs00150eopenalex-snapshot
Recent advances in well-defined, late transition metal complexes that make and/or break C–N, C–O and C–S bonds
inferred← citeshttps://doi.org/10.1039/c6ra00395hopenalex-snapshot
A facile and practical copper diacetate mediated, ligand free C–N cross coupling of trivalent organobismuth compounds with amines and N-heteroarenes
inferred← citeshttps://doi.org/10.1039/c6sc00082gopenalex-snapshot
Palladium-catalyzed difluoromethylthiolation of heteroaryl bromides, iodides, triflates and aryl iodides
inferred← citeshttps://doi.org/10.1039/c7ob00178aopenalex-snapshot
An active catalytic system for Suzuki–Miyaura cross-coupling reactions using low levels of palladium loading
inferred← citeshttps://doi.org/10.1039/c8ob02856gopenalex-snapshot
The roles of Lewis acidic additives in organotransition metal catalysis
inferred← citeshttps://doi.org/10.1039/c8qo01281dopenalex-snapshot
Nickel-promoted C(2)–H amidation of quinoline N -oxides with N -fluorobenzenesulfonimide
inferred← citeshttps://doi.org/10.1039/c9nj04076eopenalex-snapshot
An imidazolin-2-iminato ligand organozinc complex as a catalyst for hydroboration of organic nitriles
inferred← citeshttps://doi.org/10.1039/c9sc03691aopenalex-snapshot
Switching the site-selectivity of C–H activation in aryl sulfonamides containing strongly coordinating N-heterocycles
inferred← citeshttps://doi.org/10.1039/d0sc04180gopenalex-snapshot
Lewis acid-assisted Ir( iii ) reductive elimination enables construction of seven-membered-ring sulfoxides
inferred← citeshttps://doi.org/10.1039/d6cc01865copenalex-snapshot
Decarboxylative arylation and alkoxylation of pyridine-2-carboxylic acid N -oxide derivatives via electrophilic carbene: access to lucidimine E and australine
inferred← citeshttps://doi.org/10.1055/a-2849-7091openalex-snapshot
Pd-Catalyzed Buchwald–Hartwig Coupling of Imidazo[1,2-b]pyridazine with Aryl/Hetero Aryl Amines for the Synthesis of Functionalized Pyridazines
inferred← citeshttps://doi.org/10.1055/sos-sd-115-00035openalex-snapshot
15.1.4 Pyridines (Update 2016)
inferred← citeshttps://doi.org/10.1055/sos-sd-131-00012openalex-snapshot
31.42 Product Class 42: Arylphosphines and Derivatives
inferred← citeshttps://doi.org/10.1126/science.aad3087openalex-snapshot
A supramolecular microenvironment strategy for transition metal catalysis
inferred← citeshttps://doi.org/10.3390/appliedchem6030055openalex-snapshot
(Co2+,Pd2+)2SiO4Pd0 Olivine: Influence of Lewis Acids on Heterogeneous Heck–Mizoroki Catalysis
inferred← citeshttps://doi.org/10.3390/molecules190913448openalex-snapshot
Copper/N,N-Dimethylglycine Catalyzed Goldberg Reactions Between Aryl Bromides and Amides, Aryl Iodides and Secondary Acyclic Amides
inferred← citeshttps://doi.org/10.3390/molecules31132339openalex-snapshot
Mapping Regioisomer-Dependent Buchwald–Hartwig C-N Coupling: Bromoimidazo[1,5-a]pyridines as a Model Electrophile Series
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