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Copper‐Catalyzed [2+2+2] Modular Synthesis of Multisubstituted Pyridines: Alkenylation of Nitriles with Vinyliodonium Salts

https://doi.org/10.1002/anie.201700696
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What this work says

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

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[2+2+2] Cycloaddition Reactions Catalyzed by Transition Metal Complexes
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Cobalt‐katalysierte einstufige Synthese von anellierten Pyridinen
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Cobalt-vermittelte [2+2+2]-Cycloadditionen: eine ausgereifte Synthesestrategie
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Organocobaltverbindungen in der Pyridinsynthese – ein Beispiel für Struktur‐Wirkungs‐Beziehungen in der Homogenkatalyse
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A Simple and Highly Efficient Iron Catalyst for a [2+2+2] Cycloaddition to Form Pyridines
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Diverse Reactivity in a Rhodium(III)‐Catalyzed Oxidative Coupling of N‐Allyl Arenesulfonamides with Alkynes
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Synthesis of Pyridines by Carbenoid‐Mediated Ring Opening of 2H‐Azirines
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Copper(II)‐Catalyzed Three‐Component Cascade Annulation of Diaryliodoniums, Nitriles, and Alkynes: A Regioselective Synthesis of Multiply Substituted Quinolines
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Regioselektiv funktionalisierte Pyridine aus nachhaltigen Ressourcen
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Copper‐Catalyzed Intramolecular Electrophilic Carbofunctionalization of Allylic Amides
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Isothiourea‐Mediated One‐Pot Synthesis of Functionalized Pyridines
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Gold‐Catalyzed Synthesis of Functionalized Pyridines by Using 2H‐Azirines as Synthetic Equivalents of Alkenyl Nitrenes
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Metal‐Free [2+2+2] Cycloaddition of Ynamides and Nitriles: Mild and Regioselective Synthesis of Fully Substituted Pyridines
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Metal‐Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions
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A Cobalt‐Catalyzed One‐Step Synthesis of Annelated Pyridines
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Cobalt‐Mediated [2 + 2 + 2]‐Cycloadditions: A Maturing Synthetic Strategy [New Synthetic Methods (43)]
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Organocobalt Compounds in the Synthesis of Pyridines–An Example of Structure‐Effectivity Relationships in Homogeneous Catalýsis
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A Simple and Highly Efficient Iron Catalyst for a [2+2+2] Cycloaddition to Form Pyridines
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Diverse Reactivity in a Rhodium(III)‐Catalyzed Oxidative Coupling of N‐Allyl Arenesulfonamides with Alkynes
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Synthesis of Pyridines by Carbenoid‐Mediated Ring Opening of 2H‐Azirines
inferredcites →https://doi.org/10.1002/anie.201300586openalex-snapshot
Copper(II)‐Catalyzed Three‐Component Cascade Annulation of Diaryliodoniums, Nitriles, and Alkynes: A Regioselective Synthesis of Multiply Substituted Quinolines
inferredcites →https://doi.org/10.1002/anie.201301919openalex-snapshot
Regioselectively Functionalized Pyridines from Sustainable Resources
inferredcites →https://doi.org/10.1002/anie.201303724openalex-snapshot
Copper‐Catalyzed Intramolecular Electrophilic Carbofunctionalization of Allylic Amides
inferredcites →https://doi.org/10.1002/anie.201306786openalex-snapshot
Isothiourea‐Mediated One‐Pot Synthesis of Functionalized Pyridines
inferredcites →https://doi.org/10.1002/anie.201402470openalex-snapshot
Gold‐Catalyzed Synthesis of Functionalized Pyridines by Using 2H‐Azirines as Synthetic Equivalents of Alkenyl Nitrenes
inferredcites →https://doi.org/10.1002/anie.201603889openalex-snapshot
Metal‐Free [2+2+2] Cycloaddition of Ynamides and Nitriles: Mild and Regioselective Synthesis of Fully Substituted Pyridines
inferredcites →https://doi.org/10.1002/anie.201606604openalex-snapshot
Metal‐Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions
inferredcites →https://doi.org/10.1002/chem.201001100openalex-snapshot
Recent Strategies for the Synthesis of Pyridine Derivatives
inferredcites →https://doi.org/10.1002/ejoc.201100749openalex-snapshot
Tetraols as Templates for the Synthesis of Large endo‐Functionalized Macrocycles
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Discovery of novel 5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine derivatives as γ-secretase modulators (Part 2)
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Construction of fused heterocycles by metal-mediated [2+2+2] cyclotrimerization of alkynes and/or nitriles
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Synthesis and easy aromatisation of 5-substituted 6-(alkylthio)-2-methoxy-2,3-dihydropyridines. A new approach to the pyridine ring
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Titanium-Catalyzed Multicomponent Couplings: Efficient One-Pot Syntheses of Nitrogen Heterocycles
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Solvolysis of Vinyl Iodonium Salts. New Insights into Vinyl Cation Intermediates
inferredcites →https://doi.org/10.1021/cr00039a007openalex-snapshot
Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds
inferredcites →https://doi.org/10.1021/cr00089a006openalex-snapshot
Transition metal-mediated cycloaddition reactions of alkynes in organic synthesis
inferredcites →https://doi.org/10.1021/cr030677fopenalex-snapshot
Construction of Pyridine Rings by Metal-Mediated [2 + 2 + 2] Cycloaddition
inferredcites →https://doi.org/10.1021/cr200060gopenalex-snapshot
The Methylation Effect in Medicinal Chemistry
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Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition to N -Activated Pyridines
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Metal-Free Multicomponent Syntheses of Pyridines
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Solvolysis of Cyclohexenyliodonium Salt, a New Precursor for the Vinyl Cation: Remarkable Nucleofugality of the Phenyliodonio Group and Evidence for Internal Return from an Intimate Ion-Molecule Pair
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Synthesis of Pyridine-Containing Macrocycles by Cobalt-Mediated Trimerization of Triply-Bonded Species
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Cp*RuCl-Catalyzed [2 + 2 + 2] Cycloadditions of α,ω-Diynes with Electron-Deficient Carbon−Heteroatom Multiple Bonds Leading to Heterocycles
inferredcites →https://doi.org/10.1021/ja0508931openalex-snapshot
A Nickel-Catalyzed Route to Pyridines
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A Solution to the 2-Pyridyl Organometallic Cross-Coupling Problem: Regioselective Catalytic Direct Arylation of Pyridine N-Oxides
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Synthesis of Substituted Pyridine Derivatives via the Ruthenium-Catalyzed Cycloisomerization of 3-Azadienynes
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Single-Step Synthesis of Pyrimidine Derivatives
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Direct Synthesis of Pyridine Derivatives
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Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C−H Functionalization
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Synthesis of (+)-Complanadine A, an Inducer of Neurotrophic Factor Excretion
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Direct C−H Arylation of Electron-Deficient Heterocycles with Arylboronic Acids
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Enantioselective α-Arylation of Aldehydes via the Productive Merger of Iodonium Salts and Organocatalysis
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Mechanistic Understanding of the Unexpected Meta Selectivity in Copper-Catalyzed Anilide C–H Bond Arylation
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Nickel-Catalyzed Dehydrogenative [4 + 2] Cycloaddition of 1,3-Dienes with Nitriles
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Palladium-Catalyzed C–H Activation/Cross-Coupling of Pyridine N-Oxides with Nonactivated Secondary Alkyl Bromides
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Modular Pyridine Synthesis from Oximes and Enals through Synergistic Copper/Iminium Catalysis
inferredcites →https://doi.org/10.1021/ja401701xopenalex-snapshot
Synthesis of Substituted Pyridines from Cascade [1 + 5] Cycloaddition of Isonitriles to N -Formylmethyl-Substituted Enamides, Aerobic Oxidative Aromatization, and Acyl Transfer Reaction
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Copper-Catalyzed Electrophilic Carbofunctionalization of Alkynes to Highly Functionalized Tetrasubstituted Alkenes
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Copper-Catalyzed Carboarylation of Alkynes via Vinyl Cations
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Rh(III)-Catalyzed Decarboxylative Coupling of Acrylic Acids with Unsaturated Oxime Esters: Carboxylic Acids Serve as Traceless Activators
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Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C−H Activation
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Gold-Catalyzed Intermolecular Hetero-Dehydro-Diels−Alder Cycloaddition of Captodative Dienynes with Nitriles: A New Reaction and Regioselective Direct Access to Pyridines
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A Simple, Modular Synthesis of Substituted Pyridines
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One-Pot Synthesis of Highly Functionalized Pyridines via a Rhodium Carbenoid Induced Ring Expansion of Isoxazoles
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Mn(III)-Mediated Reactions of Cyclopropanols with Vinyl Azides: Synthesis of Pyridine and 2-Azabicyclo[3.3.1]non-2-en-1-ol Derivatives
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Ruthenium-Catalyzed Formal Dehydrative [4 + 2] Cycloaddition of Enamides and Alkynes for the Synthesis of Highly Substituted Pyridines: Reaction Development and Mechanistic Study
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The Medicinal Chemist’s Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates
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Synthesis of Novel Cyclic Olefin Copolymer (COC) with High Performance via Effective Copolymerization of Ethylene with Bulky Cyclic Olefin
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A Concise Construction of Polycyclic Quinolines via Annulation of ω-Cyano-1-alkynes with Diaryliodonium Salts
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Metal-free intermolecular formal cycloadditions enable an orthogonal access to nitrogen heterocycles
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A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines
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The fascinating construction of pyridine ring systems by transition metal-catalysed [2 + 2 + 2] cycloaddition reactions
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Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst
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One-pot synthesis of quinazoline derivatives via [2+2+2] cascade annulation of diaryliodonium salts and two nitriles
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C–N and C–P bond formation via cross dehydrative coupling reaction: an efficient synthesis of novel 3,4-dihydroquinazolines
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A catalyst-controlled selective synthesis of pyridines and pyrroles
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Unraveling innate substrate control in site-selective palladium-catalyzed C–H heterocycle functionalization
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Synthesis of benzo[1,3]oxazines via copper( i )-catalyzed cascade annulation of nitriles, aldehydes and diaryliodonium salts
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Pyrrole, pyrrolidine pyridine, piperidine, azepine and tropane alkaloids
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Transition-Metal-Catalyzed C-H Functionalization for the Synthesis of Substituted Pyridines
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Inter- and Intramolecular [4+2]-Cycloaddition Reactions with 4,4-Disubstituted N-Silyl-1,4-dihydropyridines as Precursors for N-Protonated 2-Azabutadiene Intermediates
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A Meta-Selective Copper-Catalyzed C–H Bond Arylation
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Synthesis of 2,2’-Bipyridines by Transition Metal-Catalyzed Alkyne/Nitrile [2 + 2 + 2] Cycloaddition Reactions

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

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Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents
inferred← citeshttps://doi.org/10.1021/acs.joc.0c02192openalex-snapshot
Palladium-Catalyzed Site-Selective Benzocyclization of Naphthoic Acids with Diaryliodonium Salts: Efficient Access to Benzanthrones
inferred← citeshttps://doi.org/10.1021/acs.joc.1c00101openalex-snapshot
Ligand-Enabled Copper-Catalyzed N-Alkynylation of Sulfonamide with Alkynyl Benziodoxolone: Synthesis of Amino Acid-Derived Ynamide
inferred← citeshttps://doi.org/10.1021/acs.joc.4c02910openalex-snapshot
Divergent Synthesis of Polysubstituted 1,2-Dihydropyridines and Pyridines through Manganese-Mediated Radical Cascade Cyclization of Tertiary Enamides
inferred← citeshttps://doi.org/10.1021/acs.joc.5c03124openalex-snapshot
[3 + 1 + 2] Annulation for Modular Synthesis of Polysubstituted Pyridines Using Calcium Carbide as an Acetylene Surrogate
inferred← citeshttps://doi.org/10.1021/acs.joc.9b02999openalex-snapshot
Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles
inferred← citeshttps://doi.org/10.1021/acs.organomet.0c00152openalex-snapshot
Regioselectivity in the Iridium-Catalyzed [2 + 2 + 2] Cycloaddition of Unsymmetrical α,ω-Diynes with Nitrile: A DFT Study
inferred← citeshttps://doi.org/10.1021/acs.orglett.0c00721openalex-snapshot
Facile Synthesis of α-Boryl-Substituted Allylboronate Esters Using Stable Bis[(pinacolato)boryl]methylzinc Reagents
inferred← citeshttps://doi.org/10.1021/acs.orglett.2c02606openalex-snapshot
Regio- and Chemoselective Copper-Catalyzed Formal [2+2+2] Cycloaddition of Primary Amines with Arylacetylenes to 2,4,5-Trisubstituted Pyridines
inferred← citeshttps://doi.org/10.1021/acs.orglett.2c04027openalex-snapshot
Visible-Light-Mediated Solvent-Switched Photosensitizer-Free Synthesis of Polyfunctionalized Quinolines and Pyridines
inferred← citeshttps://doi.org/10.1021/acs.orglett.4c03559openalex-snapshot
Highly Regioselective Modular Assembly of 3-Phosphonyl Polysubstituted Pyridines through Radical Cascade Cyclization of 1,5-Enynes with Phosphine Oxide by Photoinitiation
inferred← citeshttps://doi.org/10.1021/acs.orglett.5c02772openalex-snapshot
B2pin2-Enabled Nickel/Brønsted Acid Relay-Catalyzed Reductive [2+2+2] Cycloaddition: Facile Access to Unsymmetric Pentacyclic Pyridine Derivatives
inferred← citeshttps://doi.org/10.1021/acs.orglett.7b01701openalex-snapshot
A Modular Synthesis of 4-Aminoquinolines and [1,3] N-to-C Rearrangement to Quinolin-4-ylmethanesulfonamides
inferred← citeshttps://doi.org/10.1021/acs.orglett.7b02388openalex-snapshot
Construction of Functionalized Annulated Sulfone via SO 2 /I Exchange of Cyclic Diaryliodonium Salts
inferred← citeshttps://doi.org/10.1021/acs.orglett.8b00447openalex-snapshot
N-Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts To Generate α,β-Unsaturated Ketones
inferred← citeshttps://doi.org/10.1021/acs.orglett.8b01090openalex-snapshot
Copper-Catalyzed Ring-Expansion Cascade of Azirines with Alkynes: Synthesis of Multisubstituted Pyridines at Room Temperature
inferred← citeshttps://doi.org/10.1021/acs.orglett.8b02703openalex-snapshot
N -Silylenamines as Reactive Intermediates: Hydroamination for the Modular Synthesis of Selectively Substituted Pyridines
inferred← citeshttps://doi.org/10.1021/acscatal.1c03871openalex-snapshot
Origins of Regio- and Chemoselectivity in Iron-PDAI-Catalyzed [2+2+2] Cycloaddition Syntheses of 4,6-Disubstituted 2-Aminopyridines
inferred← citeshttps://doi.org/10.1021/acscatal.9b00470openalex-snapshot
Copper-Catalyzed Tandem O-Vinylation of Arylhydroxylamines/[3,3]-Rearrangement/Cyclization: Synthesis of Highly Substituted Indoles and Benzoindoles
inferred← citeshttps://doi.org/10.1021/acsomega.9b00728openalex-snapshot
Synthesis of Multifunctional Aryl(trifloxyalkenyl)iodonium Triflate Salts
inferred← citeshttps://doi.org/10.1038/s41467-025-59772-5openalex-snapshot
Selective radical-type perfluoro-tert-butylation of unsaturated compounds with a stable and scalable reagent
inferred← citeshttps://doi.org/10.1038/s42004-020-00343-8openalex-snapshot
Wet carbonate-promoted radical arylation of vinyl pinacolboronates with diaryliodonium salts yields substituted olefins
inferred← citeshttps://doi.org/10.1038/s42004-023-00986-3openalex-snapshot
Direct electrophilic and radical isoperfluoropropylation with i-C3F7-Iodine(III) reagent (PFPI reagent)
inferred← citeshttps://doi.org/10.1039/c8cc05307copenalex-snapshot
Cu-Catalyzed switchable synthesis of functionalized pyridines and pyrroles
inferred← citeshttps://doi.org/10.1039/c8qo00052bopenalex-snapshot
One-pot regioselective synthesis of 2,4-disubstituted quinolines via copper( ii )-catalyzed cascade annulation
inferred← citeshttps://doi.org/10.1039/c8sc01818aopenalex-snapshot
Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers
inferred← citeshttps://doi.org/10.1039/c9gc03957kopenalex-snapshot
Tandem selective reduction of nitroarenes catalyzed by palladium nanoclusters
inferred← citeshttps://doi.org/10.1039/c9qo00619bopenalex-snapshot
Utilization of nitriles as the nitrogen source: practical and economical construction of 4-aminopyrimidine and β-enaminonitrile skeletons
inferred← citeshttps://doi.org/10.1039/c9qo01259aopenalex-snapshot
Nickel( ii )-catalyzed C–C, N–C cascade coupling of ketonitriles into substituted pyrroles and pyridines
inferred← citeshttps://doi.org/10.1039/c9sc01035aopenalex-snapshot
Assembly of 1 H -isoindole derivatives by selective carbon–nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging
inferred← citeshttps://doi.org/10.1039/d0cc07547gopenalex-snapshot
Palladium-catalyzed C–H activation of simple arenes and cascade reaction with nitriles: access to 2,4,5-trisubstituted oxazoles
inferred← citeshttps://doi.org/10.1039/d0ob01055copenalex-snapshot
Copper( i )-catalyzed intermolecular cyanoarylation of alkenes: convenient access to α-alkylated arylacetonitriles
inferred← citeshttps://doi.org/10.1039/d0qo00693aopenalex-snapshot
Iron–cobalt-catalyzed heterotrimerization of alkynes and nitriles to polyfunctionalized pyridines
inferred← citeshttps://doi.org/10.1039/d0ta11503gopenalex-snapshot
Atomically dispersed cobalt on graphitic carbon nitride as a robust catalyst for selective oxidation of ethylbenzene by peroxymonosulfate
inferred← citeshttps://doi.org/10.1039/d1gc01332gopenalex-snapshot
Indium( iii )-catalyzed solvent-free multicomponent [2 + 2 + 1 + 1]-annulation to polycyclic functionalized fused pyridines as potential optical chemosensors
inferred← citeshttps://doi.org/10.1039/d1nj05433copenalex-snapshot
Cu-catalyzed [2 + 2 + 1] cascade annulation of vinyl iodonium salts with elemental sulfur/selenium for the modular synthesis of thiophenes and selenophenes
inferred← citeshttps://doi.org/10.1039/d1ob02501eopenalex-snapshot
Diaryliodonium( iii ) salts in one-pot double functionalization of C–I III and ortho C–H bonds
inferred← citeshttps://doi.org/10.1039/d2sc05903gopenalex-snapshot
Designing P-type bi-stable overcrowded alkene-based chiroptical photoswitches
inferred← citeshttps://doi.org/10.1039/d3qo00685aopenalex-snapshot
Fe(OTf) 3 -catalyzed annulation of α,β-unsaturated ketoxime acetates with enaminones for the synthesis of functionalized 2,4-diarylpyridines
inferred← citeshttps://doi.org/10.1039/d3qo01712eopenalex-snapshot
Distal iodine migration of arylalkynes via cyclic monoaryliodonium salts
inferred← citeshttps://doi.org/10.1039/d3qo01804kopenalex-snapshot
Light promoted metal-free regio- and stereoselective isoperfluoropropylation of unactivated alkenes with an i-C 3 F 7 -iodine( iii ) reagent
inferred← citeshttps://doi.org/10.1039/d4nj01648copenalex-snapshot
Cu( ii )-catalyzed annulation of α,β-unsaturated ketoxime acetates with 3-formylchromones for the synthesis of functionalized 2,4-diarylpyridines
inferred← citeshttps://doi.org/10.1039/d5cs00024fopenalex-snapshot
Recent advances in the transformation of nitriles into diverse N-heterocycles
inferred← citeshttps://doi.org/10.1055/a-2650-7789openalex-snapshot
Experimental Electrochemical Potentials of Iodine(III) Reagents
inferred← citeshttps://doi.org/10.1055/s-0036-1589515openalex-snapshot
Cu-Catalyzed Cascade Annulation of Diaryliodonium Salts and Nitriles: Synthesis of Nitrogen-Containing Heterocycles
inferred← citeshttps://doi.org/10.12677/jocr.2024.124053openalex-snapshot
Research Progress in the Synthesis of Alkenyl Hypervalent Iodine
inferred← citeshttps://doi.org/10.3389/fchem.2024.1376948openalex-snapshot
Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiols
inferred← citeshttps://doi.org/10.3390/catal15020151openalex-snapshot
Iron/Rhodium Bimetallic Lewis Acid/Transition Metal Relay Catalysis for Alkynylation/Cyclotrimerization Sequential Reactions Toward Isoindolinone Derivatives from N,O-Cyclic Acetals
inferred← citeshttps://doi.org/10.3390/molecules26113240openalex-snapshot
Preparation and Synthetic Application of Naproxen-Containing Diaryliodonium Salts
inferred← citeshttps://doi.org/10.3390/molecules28062737openalex-snapshot
Recent Advances in Synthetic Routes to Azacycles
inferred← citeshttps://doi.org/10.3390/molecules30173629openalex-snapshot
Ni-Catalyzed [2 + 2 + 2] Cycloaddition via the Capture of Azametallacyclopentadienes with Allyl Boronate: Facile Access to Fused Pyridine Derivatives
inferred← citeshttps://doi.org/10.3906/kim-2012-15openalex-snapshot
DFT (density functional theory) studies on cycloisomerization of 15–membered triazatriacetylenic macrocycle
inferred← citeshttps://doi.org/10.5059/yukigoseikyokaishi.79.766openalex-snapshot
Metal-Free Synthesis of Heterocycles via Activation of Alkynes by Hypervalent Iodine
inferred← citeshttps://doi.org/10.6023/cjoc202104007openalex-snapshot
Study on the Selective Difluorochloroethylation Reactions of Amides with Hypervalent Iodine Reagent
inferred← citeshttps://doi.org/10.6023/cjoc202106006openalex-snapshot
Recent Progress in Radical Arylation Reaction with Diaryliodonium Salts under Photocatalysis
inferred← citeshttps://doi.org/10.6023/cjoc202412026openalex-snapshot
Recent Progress in Radical Arylation Reaction Involving Diaryliodonium Salts
inferred← citeshttps://doi.org/10.9734/ajacr/2019/v4i1-230104openalex-snapshot
Salts in Organic Synthesis: An Overview and Their Diversified Use
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