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RESEARCH PAPER · Nature Catalysis · 2023

Elucidating electron-transfer events in polypyridine nickel complexes for reductive coupling reactions

Craig S. Day, Ángel Rentería‐Gómez, Stephanie J. Ton, Achyut Ranjan Gogoi, Osvaldo Gutiérrez, Rubén Martı́n

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Elucidating electron-transfer events in polypyridine nickel complexes for reductive coupling reactionsOriginalComproportionation and disproportionation in nickel and copper complexes86Overview of outer-sphere electron transfer mediators for electrosynthesis13One electron is better than two6Nickel-catalyzed reductive coupling reaction of monofluoroalkyl triflates with alkyl carboxylic acids toward the synthesis of α-alkyl-α-fluoro-alkylketones10Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp 3 –sp 2 Carbon–Carbon Bonds59Harnessing Sulfur(VI) Fluoride Exchange Click Chemistry and Photocatalysis for Deaminative Benzylic Arylation331,2‐Arylsulfonylation of Vinyl Ethers and Esters Enabled by Dual Ni Catalysis2Dual Nickel/Photoredox-Catalyzed Asymmetric Carbosulfonylation of Alkenes99Photogenerated Ni(I)–Bipyridine Halide Complexes: Structure–Function Relationships for Competitive C(sp 2 )–Cl Oxidative Addition and Dimerization Reactivity Pathways43Hydride-Free Hydrogenation: Unraveling the Mechanism of Electrocatalytic Alkyne Semihydrogenation by Nickel–Bipyridine Complexes42C(sp2)–H Hydroxylation via Catalytic 1,4-Ni Migration with N2O44Synthesis of Nickel(I)–Bromide Complexes via Oxidation and Ligand Displacement: Evaluation of Ligand Effects on Speciation and Reactivity42Intramolecular hydroamidation of alkenes enabling asymmetric synthesis of β-lactams via transposed NiH catalysis44Ligand Redox Activity of Organonickel Radical Complexes Governed by the Geometry52Generation of Thioxanthone Hydrogen Anion by Double Photoreduction and Uses for Catalytic Photoreductions20Understanding the Reaction Mechanism of Ni-Catalyzed Regio- and Enantioselective Hydroalkylation of Enamines: Chemoselectivity of (Bi-oxazoline)NiH2Electroactive Polymers for On‐Demand Drug Release74Nickel-Catalyzed Reductive Allylation of Aldehydes with Allylic Alcohols in the Presence of CO214Nickel-Catalyzed Radical Mechanisms: Informing Cross-Coupling for Synthesizing Non-Canonical Biomolecules125Ligand Relay for Nickel‐Catalyzed Decarbonylative Alkylation of Aroyl Chlorides29Steering single-site metallaphotocatalytic pathway by accumulated electron on carbon nitride support5Roles of the Comproportionation Reaction in SO 2 Reduction Using Methane for the Flexible Recovery of Elemental Sulfur or Sulfides16Electrosynthesis of iminophosphoranes and applications in nickel catalysis18Mechanistic insights into facilitating reductive elimination from Ni( ii ) species16Ni(2,2′:6′,2′′-terpyridine) 2 : a high-spin octahedral formal Ni(0) complex2Ni(I) complexes relevant to synthetic organic catalysis0Nickel-catalysed chelation-assisted reductive defluorinative sulfenylation of trifluoropropionic acid derivatives9Kinetically-Controlled Ni-Catalyzed Direct Carboxylation of Unactivated Secondary Alkyl Bromides without Chain Walking38Nickel-Catalyzed Synthesis of Benzylamines from (Hetero)aryl Halides and Glycine-Derived N-Hydroxyphthalimide Esters4Electrophotocatalytic hydrogenation of imines and reductive functionalization of aryl halides33Nickel and Chiral Phosphoric Acid Cocatalysis Enables Synthesis of C-Acyl Glycosides16Electron transfer tuned by pressure-dependent aggregation-induced emission in InP/ZnS quantum dot–anthraquinone complexes13Enantioselective C(sp 2 )–C(sp 3 ) Bond Construction by Ni Catalysis119ProPhos: A Ligand for Promoting Nickel-Catalyzed Suzuki-Miyaura Coupling Inspired by Mechanistic Insights into Transmetalation60Advances in understanding comproportionation and disproportionation in nickel catalysis6Achieving Nickel-Catalyzed Reductive C(sp2)–B Coupling of Bromoboranes via Reversing the Activation Sequence21Nickel-Catalyzed Mono- and Dihydrosilylation of Aliphatic Alkynes in Aqueous and Aerobic Conditions16Nickel-catalyzed reductive formylation of aryl halides via formyl radical14Alkyl Cyclopropyl Ketones in Catalytic Formal [3 + 2] Cycloadditions: The Role of SmI 2 Catalyst Stabilization32Electrocatalytic Formal C(sp 2 )−H Alkylations via Nickel‐Catalyzed Cross‐Electrophile Coupling with Versatile Arylsulfonium Salts34Elektrokatalytische formale C(sp2)−H Alkylierung via Nickel‐katalysierter elektrophiler Kreuzkupplung mit vielseitigen Arylsulfoniumsalzen0Enantioselective Access to β-Amino Carbonyls via Ni-Catalyzed Formal Olefin Hydroamidation32Zinc and manganese redox potentials in organic solvents and their influence on nickel-catalyzed cross-electrophile coupling4Mechanisms of Photoredox Catalysis Featuring Nickel–Bipyridine Complexes80Nickel-Catalyzed Hydrocarboxylation of Terminal Unactivated Alkenes: Formation of Branched Carboxylic Acids and Competing Catalyst Deactivation from CO2 Reduction to CO4Chromium‐ and Metal‐Reductant‐Free Asymmetric Nozaki–Hiyama–Kishi (NHK) Reaction Enabled by Metallaphotoredox Catalysis21Chromium‐ and Metal‐Reductant‐Free Asymmetric Nozaki–Hiyama–Kishi (NHK) Reaction Enabled by Metallaphotoredox Catalysis5Ni(3,5-CF3stb)2(Et2O): A “Super-Naked” Nickel Complex5Late-Stage C( sp 2 )–C( sp 3 ) Diversification via Nickel Oxidative Addition Complexes12Photoredox/Nickel Dual-Catalyzed Allylation of Aldehydes with Allylic Alcohols and Mechanistic Insights in the Presence of CO 215A Compendium of Methodically Determined Ground‐ and Excited‐State Properties of Homoleptic Ruthenium(II) and Osmium(II) Photosensitizers21Intermolecular Regioselective Alkylarylation of Vinylarenes via Photoredox/Nickel Dual Catalysis9Bis[μ-3-(pyridin-2-yl)pyrazolato]bis[acetato(3,5-dimethyl-1 H -pyrazole)nickel(II)]0Zinc and manganese redox potentials in organic solvents and their influence on nickel-catalysed cross-electrophile coupling89Redox Activity and Potentials of Bidentate N‐Ligands Commonly Applied in Nickel‐Catalyzed Cross‐Coupling Reactions0Redox Activity and Potentials of Bidentate N‐Ligands Commonly Applied in Nickel‐Catalyzed Cross‐Coupling Reactions14Electrochemical Nickel-Catalyzed Synthesis of Unsymmetrical Diorganyl Selanes from Diaryl Diselanes and Aryl and Alkyl Iodides3Ni-catalysed remote C(sp3)–H functionalization using chain-walking strategies60Ni-catalyzed reductive cyanation of alkenyl tosylates and triflates5Modular Assembly of E -Selective Trisubstituted Alkenylborons via Nickel-Catalyzed Reductive Dicarbofunctionalization of Ethynylboron5Nickel-catalyzed cyanation of C—S bond using CO2 and NH34A nickel metalloradical bearing a phenalenyl-based tridentate ligand3Nickel-Catalyzed Asymmetric Homobenzylic Hydroamidation of Vinylarenes: A Strategy for Chiral β-(Hetero)arylethylamides0Enhanced Proton-Coupled Electron-Transfer Reactivity by a Mononuclear Nickel(II) Hydroxide Radical Complex5Ni-Catalyzed Enantioconvergent Kumada–Corriu Cross-Coupling between β-Bromostyrenes and Secondary Grignard Reagents: Reaction Development, Scope and Mechanistic Investigations7Selective Ni-Catalyzed Cross-Electrophile Coupling of Heteroaryl Chlorides and Aryl Bromides at 1:1 Substrate Ratio20Synthesis and characterization of alkali metal salts bearing a phenalenyl-based tridentate ligand2Cationic nickel(II) complexes bearing a phenalenyl-based tridentate ligand1Electrochemical Ni–H catalysis for selective tail-to-tail reductive dimerization of terminal alkynes to access 2,3-dibranched butadienes1Synergistic Ni/Co catalysis in C(sp 2 )–C(sp 3 ) reductive coupling: a DFT study0Electrochemical Nickel-Catalyzed C(sp2)-H Functionalization of Tropones with Aldehydes6Nickel-Catalyzed Asymmetric Homobenzylic Hydroamidation of Aryl Alkenes to Access Chiral β-Arylamides27Asymmetric reductive arylation and alkenylation to access S-chirogenic sulfinamides41Sulfhydryl group modified layered double hydroxide accelerates the formation of NiOOH active phase for enhanced urea oxidation reaction1Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents10Nickel-catalyzed electrochemical carboxylation of propargylic esters with CO2 to 2,3-allenoic acids7Evidence for a Unifying NiI/NiIII Mechanism in Light-Mediated Cross-Coupling Catalysis24Photoelectrochemical Iron(III) Catalysis for Late‐Stage C─H Fluoroalkylations26Photoelektrochemische Eisen(III)‐Katalyse für C─H‐Fluoralkylierungen im synthetischen Spätstadium1Regioselective Transformations of Unsaturated Systems Catalyzed by Low-Valent Nickel: Cycloaddition, Hydrosilylation, and Dicarbofunctionalization1Nickel‐Catalyzed Cross‐Electrophile Coupling to Access Polysubstituted Cyclobutenes7Nickel‐Catalyzed Cross‐Electrophile Coupling to Access Polysubstituted Cyclobutenes0Rapid Oxygen Atom Transfer at a Catalysis-Relevant Ni(I)–Alkyl Complex with N 2 O10Nickel-Based Photocatalyst: From Structure to Application15Discovery of Ni(I) Complexes for CO2 Insertion Enabled by a Machine Learning-Computational-Selection Sequence122-Substituted vs 2,9-Disubstituted Phenanthroline-NiII-halides: Speciation Control and Structural Elucidation in Solution0Unveiling the Switchable Chemoselectivity Mechanism in Electrochemical Nickel-Catalyzed C(sp2)–O Coupling of Phenols and Aliphatic Alcohols6Photochemical Nickel‐Catalyzed Hydrocyanation of Unactivated Alkenes Using Isonitriles †2Reactivity Studies of Bipyridine-Ligated Nickel(I) and Nickel(0) Complexes Inform the Mechanism in Modern Cross-Coupling Reactions28Nickel/Light-Driven Catalysis Enables Site-Selective Sulfoximination of Electron-Rich Arenes4Ni/Chiral Phosphoric Acid Cooperative Catalysis Enabled Radical Coupling of Carboxylic Esters/Amides to C‐ Acyl Glycosides3Dinuclear Ni enabled reductive diarylation of dienes: Intramolecular comproportionation as the key mechanistic driver1Advances in NiI/NiIII-Catalyzed C(sp2)–Heteroatom Cross-Couplings15Photocatalytic C(sp 2 )—C(sp 3 ) Cross-Coupling between C(sp 2 )—Cl Bond and C(sp 3 )—H Bond0Ring-opening decarbonylative C(sp 3 )–C(sp 3 ) cross-electrophile coupling of cyclic imides with unactivated alkyl chlorides0Cross-Electrophile Coupling of N -Hydroxyphthalimide Esters with Aryl Bromides Using an Inner-Sphere Homogeneous Reductant7Nickel-Catalyzed Reductive Arylation of N -Acyl Hemiaminals0Electrophotochemical Decarboxylative C−H Fluoroalkylation via a Fe 2 O 3 −FTO Active Photoanode4Electronickel‐Catalyzed Stereoselective Synthesis of Butafulvenes2Transition-Metal Hydride Catalysis Meets Nitrenoid Transfer: Design Principles for Precision C–N Bond Formation9Cross- and branched-selective hydroalkenylation by metal hydride selection9Electronickel‐Catalyzed Stereoselective Synthesis of Butafulvenes0Nickel-Catalyzed Cross-Dehydrogenative Allylation of Aldehydes10Controlling the Redox Speciation of N,C,N–Bi Complexes Using the Anion Coordination Index0Nickel-Catalyzed Selective Defluorinative Deuteration of Polyfluoroarenes2Investigation of electrocatalytic semi-hydrogenation catalyzed by nickel complexes0Nickel-Catalyzed Regio- and Stereoselective Alkylation and Dimerization of Allenes: Harnessing the Flexibility of Nickel Oxidation States in Reductive Allene Coupling0Enantioconvergent Decarboxylative Arylation of Serine and Isoserine Derivatives with Aryl Halides: Modular Access to Chiral 1,2-Amino Alcohols1Ni–Ir Interaction Enables a Dark Reactive State in Nickel Catalysis0Suzuki–Miyaura Cross-Coupling Using Ketones for the Synthesis of Multisubstituted Alkenes0“Store-and-Release” Strategy Enables Nickel-Catalyzed Deaminative Migratory Arylation of Aliphatic Amines0Ligand design broadens NiI-catalysed C(sp2)–heteroatom couplings of aryl bromides at low catalyst loadings0

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  49. Late-Stage C( sp 2 )–C( sp 3 ) Diversification via Nickel Oxidative Addition Complexes

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