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Selective Three-Component Reductive Alkylalkenylation of Unbiased Alkenes via Carbonyl-Directed Nickel Catalysis

https://doi.org/10.1021/acscatal.2c02163

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What this work says

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

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Catalytic Asymmetric Synthesis

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Asymmetric Hydrovinylation: New Perspectives through Use of Modular Ligand Systems

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A Copper Catalyst with a Cinchona‐Alkaloid‐Based Sulfonamide Ligand for Asymmetric Radical Oxytrifluoromethylation of Alkenyl Oximes

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Synthesis of Functionalized α‐Vinyl Aldehydes from Enaminones

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Nickel‐Catalyzed 1,2‐Diarylation of Alkenyl Carboxylates: A Gateway to 1,2,3‐Trifunctionalized Building Blocks

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Pd(II)‐Catalyzed Tandem Enantioselective Methylene C(sp 3 )−H Alkenylation–Aza‐Wacker Cyclization to Access β‐Stereogenic γ‐Lactams

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Nickel‐Catalyzed Regioselective Alkenylarylation of γ,δ‐Alkenyl Ketones via Carbonyl Coordination

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Transition‐Metal‐Catalyzed Three‐Component Difunctionalizations of Alkenes

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Highly Enantioselective Hydrogenation of 1‐Alkylvinyl Benzoates: A Simple, Nonenzymatic Access to Chiral 2‐Alkanols

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Reductive Cross‐Coupling Reactions between Two Electrophiles

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Nickel‐Catalyzed Dicarbofunctionalization of Alkenes†

inferredcites →https://doi.org/10.1002/tcr.201700098openalex-snapshot

Transition Metal‐Catalyzed Dicarbofunctionalization of Unactivated Olefins

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Broadly Applicable Directed Catalytic Reductive Difunctionalization of Alkenyl Carbonyl Compounds

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Developments in Photoredox/Nickel Dual-Catalyzed 1,2-Difunctionalizations

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Nickel Catalysis in Organic Synthesis: Methods and Reactions

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Palladium-catalyzed tandem assembly of norbornene, vinylic halides, and cyanide nucleophile leading to cis-exo-2,3-disubstituted norbornanes

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Cross-Electrophile Couplings of Activated and Sterically Hindered Halides and Alcohol Derivatives

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Transition Metal (Ni, Cu, Pd)-Catalyzed Alkene Dicarbofunctionalization Reactions

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Methods and Mechanisms for Cross-Electrophile Coupling of Csp2 Halides with Alkyl Electrophiles

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Copper-Catalyzed Radical Relay for Asymmetric Radical Transformations

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Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C–C Bonds

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Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

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U.S. FDA Approved Drugs from 2015–June 2020: A Perspective

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Strategies toward Dicarbofunctionalization of Unactivated Olefins by Combined Heck Carbometalation and Cross-Coupling

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Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems

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Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides

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Pd-Catalyzed Regioselective 1,2-Difunctionalization of Vinylarenes with Alkenyl Triflates and Aryl Boronic Acids at Ambient Temperature

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Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones

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Selective, Intermolecular Alkylarylation of Alkenes via Photoredox/Nickel Dual Catalysis

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Nickel-Catalyzed Reductive 1,2-Dialkynylation of Alkenes Bearing an 8-Aminoquinoline Directing Group

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Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions

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Nickel-Catalyzed Dicarbofunctionalization of Alkenes

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Stereo- and Enantioselective Benzylic C–H Alkenylation via Photoredox/Nickel Dual Catalysis

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Stereodivergent Synthesis of BothZ- andE-Alkenes by Photoinduced, Ni-Catalyzed Enantioselective C(sp3)–H Alkenylation

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Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis

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Nickel-Catalyzed Enantioselective Reductive Aryl Fluoroalkenylation of Alkenes

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Ni(I)-Catalyzed β,δ-Vinylarylation of γ,δ-Alkenyl α-Cyanocarboxylic Esters via Contraction of Transient Nickellacycles

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Mechanistically Driven Development of Iridium Catalysts for Asymmetric Allylic Substitution

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The Asymmetric Intramolecular Heck Reaction in Natural Product Total Synthesis

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Asymmetric Hydrovinylation Reaction

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Diastereoselective Allylation of Carbonyl Compounds and Imines: Application to the Synthesis of Natural Products

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A Warning on the Use of Radical Traps as a Test for Radical Mechanisms: They React with Palladium Hydrido Complexes

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Asymmetric Conjugate Alkenylation of Enones Catalyzed by Chiral Diols

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Enantioselective Organo-SOMO Catalysis: The α-Vinylation of Aldehydes

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Enantioselective Alkenylation via Nickel-Catalyzed Cross-Coupling with Organozirconium Reagents

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A Palladium-Catalyzed Three-Component Cross-Coupling of Conjugated Dienes or Terminal Alkenes with Vinyl Triflates and Boronic Acids

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Catalytic Asymmetric Synthesis of Secondary Nitriles via Stereoconvergent Negishi Arylations and Alkenylations of Racemic α-Bromonitriles

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Palladium-Catalyzed 1,1-Difunctionalization of Ethylene

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Palladium-Catalyzed 1,4-Difunctionalization of Butadiene To Form Skipped Polyenes

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Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones

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Bimetallic Oxidative Addition Involving Radical Intermediates in Nickel-Catalyzed Alkyl–Alkyl Kumada Coupling Reactions

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Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles

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Catalytic Asymmetric Hiyama Cross-Couplings of Racemic α-Bromo Esters

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Asymmetric Organocatalytic Formal Alkynylation and Alkenylation of α,β-Unsaturated Aldehydes

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Chiral Metallacycles as Catalysts for Asymmetric Conjugate Addition of Styrylboronic Acids to α,β-Enones

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Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins through Nickel-Catalyzed Cross-Electrophile Coupling

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General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis

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Chemoselective Union of Olefins, Organohalides, and Redox-Active Esters Enables Regioselective Alkene Dialkylation

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Enantioselective Reductive Divinylation of Unactivated Alkenes by Nickel-Catalyzed Cyclization Coupling Reaction

inferredcites →https://doi.org/10.1021/jacs.1c07139openalex-snapshot

Reactivity of (bi-Oxazoline)organonickel Complexes and Revision of a Catalytic Mechanism

inferredcites →https://doi.org/10.1021/jacs.6b06285openalex-snapshot

Transition-Metal-Free Stereospecific Cross-Coupling with Alkenylboronic Acids as Nucleophiles

inferredcites →https://doi.org/10.1021/jacs.6b09170openalex-snapshot

β,γ-Vicinal Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Directed Nucleopalladation

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Mechanistic Study of an Improved Ni Precatalyst for Suzuki–Miyaura Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species

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Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes

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Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling

inferredcites →https://doi.org/10.1021/jacs.7b11707openalex-snapshot

Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling

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Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles: Rapid Access to Remotely Diarylated Ketones

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Synergistic Bimetallic Ni/Ag and Ni/Cu Catalysis for Regioselective γ,δ-Diarylation of Alkenyl Ketimines: Addressing β-H Elimination by in Situ Generation of Cationic Ni(II) Catalysts

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Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides

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Ni-Catalyzed Reductive Dicarbofunctionalization of Nonactivated Alkenes: Scope and Mechanistic Insights

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Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes

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Mechanistic Investigation of Enantioconvergent Kumada Reactions of Racemic α-Bromoketones Catalyzed by a Nickel/Bis(oxazoline) Complex

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Mechanism of Ni-Catalyzed Reductive 1,2-Dicarbofunctionalization of Alkenes

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Asymmetric Allylic Alkylation, an Enabling Methodology

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Cross-Electrophile Coupling: Principles of Reactivity and Selectivity

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Precision Ethylene/Vinyl Chloride Polymers via Condensation Polymerization

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Asymmetric 1,2-Reduction of Enones with Potassium Borohydride Catalyzed by Chiral N,N′-Dioxide–Scandium(III) Complexes

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Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay

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Quaternary stereocentres via catalytic enantioconvergent nucleophilic substitution reactions of tertiary alkyl halides

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Cobalt-catalysed enantioselective C(sp3)–C(sp3) coupling

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Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds

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Recent advances in copper-catalysed radical-involved asymmetric 1,2-difunctionalization of alkenes

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Recent developments in nickel-catalyzed intermolecular dicarbofunctionalization of alkenes

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Catalytic three-component dicarbofunctionalization reactions involving radical capture by nickel

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Classics in Stereoselective Synthesis

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Visible-light-induced bromoetherification of alkenols for the synthesis of β-bromotetrahydrofurans and -tetrahydropyrans

What points at this work

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

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Nickel‐Catalyzed Markovnikov‐Selective Hydrodifluoromethylation of Alkynes Using BrCF2H

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Nickel‐Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp3)−C(sp3) Bonds Across Alkenes**

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Reversible Radical Addition Guides Selective Photocatalytic Intermolecular Thiol‐Yne‐Ene Molecular Assembly

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Catalytic Asymmetric Synthesis of Chiral Allenylic Fluorides Enabled by Multiple Radical Sorting

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Directed Asymmetric Nickel‐Catalyzed Reductive 1,2‐Diarylation of Electronically Unactivated Alkenes

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Nickel‐Catalyzed Markovnikov‐Selective Hydrodifluoromethylation of Alkynes Using BrCF2H

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Nickel‐Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp 3 )−C(sp 3 ) Bonds Across Alkenes**

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Reversible Radical Addition Guides Selective Photocatalytic Intermolecular Thiol‐Yne‐Ene Molecular Assembly

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Ni‐Catalyzed Linearizable Cyclization/Coupling with Detachable Silicon‐Oxygen Linker: Access to 1,2‐Oxasilolanes, 3‐Hydroxysilanes and 4‐Arylalkanols

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Catalytic Asymmetric Synthesis of Chiral Allenylic Fluorides Enabled by Multiple Radical Sorting

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Enantioselective Ni‐Catalyzed Three‐Component Dicarbofunctionalization of Alkenes

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Ni-catalyzed 1,2-diarylation of unactivated alkenes directed by diverse azaheterocycles

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Ball-milling-enabled nickel-catalyzed radical relayed reductive cross-coupling

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Iron-Mediated Dialkylation of Alkenylarenes with Benzyl Bromides

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Copper-Catalyzed Hydroxyperfluoroalkylation of Unactivated Alkenes: Access to β-Perfluoroalkyl Alcohols

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inferred← citeshttps://doi.org/10.1021/acs.orglett.5c05222openalex-snapshot

Nickel-Catalyzed Enantioselective Reductive Alkenylation of N -Pyridyl Aldimines via a Mechanism of Elementary 1,4-Addition

inferred← citeshttps://doi.org/10.1021/acscatal.2c05438openalex-snapshot

Cobalt-Catalyzed Asymmetric Reductive Dicarbofunctionalization of 1,3-Dienes with o -Bromoaryl Imines as a Bis-Electrophile

inferred← citeshttps://doi.org/10.1021/acscatal.3c05690openalex-snapshot

Iron-Catalyzed Regioselective Reductive Fluoroalkylalkenylation of Unactivated Alkenes

inferred← citeshttps://doi.org/10.1021/acscatal.4c01263openalex-snapshot

Enantioselective Reductive Conjugate Alkenylation of α,β-Unsaturated Ketones and Amides via Nickel Catalysis

inferred← citeshttps://doi.org/10.1021/acscatal.4c04316openalex-snapshot

Metallaphotoredox-Catalyzed Three-Component Asymmetric Cross-Electrophile Coupling for Chiral Boronate Synthesis

inferred← citeshttps://doi.org/10.1021/acscatal.4c04371openalex-snapshot

Enantio- and Regioselective Ni-Catalyzed Radical Relay 1,4-Arylalkylation of 1,3-Enynes to Access Chiral Tetrasubstituted Allenes

inferred← citeshttps://doi.org/10.1021/acscatal.4c06641openalex-snapshot

Copper-Catalyzed Enantioselective Three-Component Fluoroalkylalkynylation of Unactivated Alkenes

inferred← citeshttps://doi.org/10.1021/acscatal.6c00696openalex-snapshot

Catalytic Enantioselective Addition of Aromatic, Heteroaryl, and Alkenyl Halides to N -Boc and N -Cbz Aldimines: Entatic States in Transition Metal Catalysis

inferred← citeshttps://doi.org/10.1021/jacs.4c01506openalex-snapshot

Selective Hydrofunctionalization of Alkenyl Fluorides Enabled by Nickel-Catalyzed Hydrogen Atoms and Group Transfer: Reaction Development and Mechanistic Study

inferred← citeshttps://doi.org/10.1021/jacs.4c12334openalex-snapshot

Ni-Catalyzed Regioselective Alkylarylation of Unactivated Alkenes in Amines Enabled by Cooperative Ligand Effects of Nitriles and Electron-Deficient Alkenes

inferred← citeshttps://doi.org/10.1021/jacs.6c07942openalex-snapshot

Direct α-Trifluoromethyl Amidation and Three-Component Alkene Trifluoroalkylamidation via Merging Halogen-Atom Transfer and Nickel-Mediated Nitrenoid Transfer

inferred← citeshttps://doi.org/10.1021/jacs.6c10952openalex-snapshot

Modular Platform for Directing-Group-Free Radical Dicarbofunctionalization of Unactivated Alkenes via Dual Nickel/Energy-Transfer Catalysis

inferred← citeshttps://doi.org/10.1038/s41467-024-45867-yopenalex-snapshot

Iron-catalyzed fluoroalkylative alkylsulfonylation of alkenes via radical-anion relay

inferred← citeshttps://doi.org/10.1038/s41467-025-68006-7openalex-snapshot

Palladium-catalyzed asymmetric migratory diarylation of unactivated directing-group-free internal alkenes

inferred← citeshttps://doi.org/10.1038/s41467-026-69838-7openalex-snapshot

Stereoselective vicinal C(sp³)–C bond formation via metallaphotoredox 1,2-difunctionalization of internal alkenes

inferred← citeshttps://doi.org/10.1038/s41929-024-01153-0openalex-snapshot

Nickel-catalysed enantioselective alkene dicarbofunctionalization enabled by photochemical aliphatic C–H bond activation

inferred← citeshttps://doi.org/10.1038/s41929-024-01211-7openalex-snapshot

Overcoming limitations in non-activated alkene cross-coupling with nickel catalysis and anionic ligands

inferred← citeshttps://doi.org/10.1039/d3sc04645aopenalex-snapshot

Divergent 1,2-carboallylation of terminal alkynes enabled by metallaphotoredox catalysis with switchable triplet energy transfer

inferred← citeshttps://doi.org/10.1039/d4cc05026fopenalex-snapshot

Direct alkene functionalization via photocatalytic hydrogen atom transfer from C(sp 3 )–H compounds: a route to pharmaceutically important molecules

inferred← citeshttps://doi.org/10.1039/d4cc06253aopenalex-snapshot

Nickel-catalyzed reductive cross-coupling of difluoromethylated secondary alkyl bromides with organohalides

inferred← citeshttps://doi.org/10.1039/d4qo02032dopenalex-snapshot

Nickel-catalyzed reductive difunctionalization of BN-heterocyclic olefins

inferred← citeshttps://doi.org/10.1039/d4sc04561kopenalex-snapshot

Ni-catalyzed enantioselective three-component reductive alkylacylation of alkenes: modular access to structurally complex α-amino ketones

inferred← citeshttps://doi.org/10.1039/d5qo01578bopenalex-snapshot

Benzophenone-catalyzed alkenylative pyridylation of vinylarenes with alkenylboronic esters

inferred← citeshttps://doi.org/10.1055/a-2192-7085openalex-snapshot

Quinolinamide-Enabled Nickel-Catalyzed Regio- and Diastereoselective γ,δ-Arylalkylation of Nonactivated Alkenes

inferred← citeshttps://doi.org/10.26434/chemrxiv-2023-bczdmopenalex-snapshot

Room Temperature Electroreductive Carboxylation of Unactivated Alkyl Chlorides with CO2 Using a Ni(II) NNN-Pincer Complex. Towards Polyvinyl chloride (PVC) Upgrading

inferred← citeshttps://doi.org/10.26434/chemrxiv-2023-dghwgopenalex-snapshot

Ni-Catalyzed Linearizable Cyclization/Alkylmetal Interception with Silicon-Oxygen as a Detachable Linker: Regioselective Access to 1,2-Oxasilolane Heterocycles, 3-Hydroxysilanes and 4-Arylalkanols

inferred← citeshttps://doi.org/10.26434/chemrxiv-2024-rf0jnopenalex-snapshot

Ni-Catalyzed Enantioselective Three-Component Reductive Alkylacylation of Enamides

inferred← citeshttps://doi.org/10.6023/cjoc202306006openalex-snapshot

Exploration of Quinim Ligand in Ni-Catalyzed Enantioselective Reductive Carbamoyl-Alkylation of Alkene

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