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RESEARCH PAPER · Catalysis Science & Technology · 2021

Reactions of nickel(0) with organochlorides, organobromides, and organoiodides: mechanisms and structure/reactivity relationships

Megan Greaves, Elliot L. B. Johnson Humphrey, David J. Nelson

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Reactions of nickel(0) with organochlorides, organobromides, and organoiodides: mechanisms and structure/reactivity relationshipsOriginalInhibition of (dppf)nickel-catalysed Suzuki–Miyaura cross-coupling reactions by α-halo-N-heterocycles22Selective synthesis of fluorinated biaryls by [MCl 2 (PhPEWO-F)] (M = Ni, Pd) catalysed Negishi cross-coupling8The Effect of Added Ligands on the Reactions of [Ni(COD)(dppf)] with Alkyl Halides: Halide Abstraction can be Reversible0The Effect of Added Ligands on the Reactions of [Ni(COD)(dppf)] with Alkyl Halides: Halide Abstraction May Be Reversible18Lewis Acid‐Promoted Oxidative Addition at a [Ni 0 (diphosphine) 2 ] Complex: The Critical Role of a Secondary Coordination Sphere25Stereoconvergent and -divergent Synthesis of Tetrasubstituted Alkenes by Nickel-Catalyzed Cross-Couplings87A guide to secondary coordination sphere editing149Mechanistic views and computational studies on transition-metal-catalyzed reductive coupling reactions48Ni-Catalysed intramolecular reductive aminocarbonylation of 2-haloaryl-tethered nitroarenes for the synthesis of dibenzazepine-based heterocycles16Nickel(Ii) Phosphine-Catalysed Hydrodehalogenation of Aryl Halides Under Mild Ambient Conditions0Nickel and Palladium Catalysis: Stronger Demand than Ever249Mapping Dual‐Base‐Enabled Nickel‐Catalyzed Aryl Amidations: Application in the Synthesis of 4‐Quinolones4Mapping Dual‐Base‐Enabled Nickel‐Catalyzed Aryl Amidations: Application in the Synthesis of 4‐Quinolones32Nickel (0) Complexes as Promising Chemosensors for Detecting the “Cork Taint” in Wine2Exterior decorating: Lewis acid secondary coordination spheres for cooperative reactivity41Photoredox Activation of Inert Alkyl Chlorides for the Reductive Cross‐Coupling with Aromatic Alkenes33Photoredox Activation of Inert Alkyl Chlorides for the Reductive Cross‐Coupling with Aromatic Alkenes6Nickel(II) phosphine-catalysed hydrodehalogenation of aryl halides under mild ambient conditions5Ligand-Based Control of Nickel Catalysts: Switching Chemoselectivity from One-Electron to Two-Electron Pathways in Competing Reactions of 4-Halotetrahydropyrans7Selective Nickel-Catalyzed Hydrodefluorination of Amides Using Sodium Borohydride12Three-Electron Nickel(I)/Nickel(0) Half-Bond5Structure–Reactivity Relationships of Buchwald-Type Phosphines in Nickel-Catalyzed Cross-Couplings741,1′‐Bis(diphenylphosphino)ferrocene0Nickel Catalysis via S H 2 Homolytic Substitution: The Double Decarboxylative Cross-Coupling of Aliphatic Acids152A Decarboxylative Cross-Coupling Platform To Access 2-Heteroaryl Azetidines: Building Blocks with Application in Medicinal Chemistry15Theoretical investigation of mechanism on nickel-catalyzed electrochemical cross-coupling of aryl bromides and arylamines1Photocatalytic C–O Coupling Enzymes That Operate via Intramolecular Electron Transfer38Nickel Complexes of Allyl and Vinyldiphenylphosphine1Interrogating the Mechanistic Features of Ni(I)-Mediated Aryl Iodide Oxidative Addition Using Electroanalytical and Statistical Modeling Techniques83Nickel Complexes of Allyl and Vinyldiphenylphosphine7A Simple Protocol for the C−N Cross‐Coupling of Aryl Chlorides with Amines Applying Ni/NHC Catalysis9Stability and C–H Bond Activation Reactions of Palladium(I) and Platinum(I) Metalloradicals: Carbon-to-Metal H-Atom Transfer and an Organometallic Radical Rebound Mechanism29Electrochemical Nickel-Catalyzed C(sp3)–C(sp3) Cross-Coupling of Alkyl Halides with Alkyl Tosylates67Recent advances in catalytic and electrocatalytic applications of half‐sandwich nickel(0/II) N–heterocyclic carbene complexes11Branched-Selective Cross-Electrophile Coupling of 2-Alkyl Aziridines and (Hetero)aryl Iodides Using Ti/Ni Catalysis54A tale of two metals: The Mizoroki-Heck reaction as a guide to compare the chemical characters of nickel and palladium in catalysis2Ligand redistribution hinders preparation of a nickel(II)-hydroxo0Computational Methods Enable the Prediction of Improved Catalysts for Nickel-Catalyzed Cross-Electrophile Coupling41Nickel-Catalyzed Arylation/Lactonization Cascade Reactions for the Synthesis of Bicyclo[3.2.1]lactones2Engaging Alkenes in Metallaphotoredox: A Triple Catalytic, Radical Sorting Approach to Olefin-Alcohol Cross-Coupling75Chemo- and Regioselective Nickel-Catalyzed Reductive 1,4-Alkylarylation of 1,3-Enynes through an L2NiAr Intermediate24Boryl radical-mediated halogen-atom transfer enables arylation of alkyl halides with electrophilic and nucleophilic coupling partners63Computational Study of the Ir-Catalyzed Formation of Allyl Carbamates from CO20A Strategy for the Formal C−N Cross‐Coupling of Tertiary Amines1A Strategy for the Formal C−N Cross‐Coupling of Tertiary Amines6Bis(benzimidazolin-2-ylidenes): Exploring the Impact of Ligand Properties in the Nickel-Catalyzed Suzuki–Miyaura Coupling5A decarbonylative approach to alkylnickel intermediates and C(sp 3 )-C(sp 3 ) bond formation57Mapping Electrophile Chemoselectivity in DalPhos/Nickel N‐Arylation Catalysis: The Unusual Influence of Remote Sterics2Varying Lewis Acidity, Covalency, and Halide Mobility to Govern Oxidative Addition Reactivity of Ni–Group 13 Bimetallic Complexes4Decarboxylative Cross-Coupling Enabled by Fe and Ni Metallaphotoredox Catalysis67Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis312Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Alkyl Halides: Mechanism-Informed Design of More General Conditions23Intramolecular Agostic Interactions and Dynamics of a Methyl Group at a Preorganized Dinickel(II) Site4Efficient Nickel Precatalysts for Suzuki‐Miyaura Cross‐Coupling of Aryl Chlorides and Arylboronic Acids Under Mild Conditions19Efficient Nickel Precatalysts for Suzuki‐Miyaura Cross‐Coupling of Aryl Chlorides and Arylboronic Acids Under Mild Conditions0Palladium‐Catalyzed Alkyl Amination of Olefins via Radical‐Polar Crossover at Room Temperature16Palladium‐Catalyzed Alkyl Amination of Olefins via Radical‐Polar Crossover at Room Temperature3Desulfonylative Suzuki–Miyaura Cross-Coupling of Unactivated Aryl Sulfones through Ni Catalysis8Rapid Methylation of Aryl Bromides Using Air‐Stable DABCO‐Bis(Trimethylaluminum) via Nickel Metallaphotoredox Catalysis0Rapid Methylation of Aryl Bromides Using Air‐Stable DABCO‐Bis(Trimethylaluminum) via Nickel Metallaphotoredox Catalysis9Carbenes and Nitrenes0NiH‐Catalyzed Enantio‐ and Regioselective Hydroarylation of Unactivated Alkenes Enabled by Outer‐Sphere Electron Transfer with Diaryliodonium Salts8NiH‐Catalyzed Enantio‐ and Regioselective Hydroarylation of Unactivated Alkenes Enabled by Outer‐Sphere Electron Transfer with Diaryliodonium Salts0C(sp 2 )─H Bond Activation with a Heterometallic Nickel–Aluminium Complex2C(sp 2 )─H Bond Activation with a Heterometallic Nickel–Aluminium Complex15Dynamics 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 Metalloradicals1Nickel‐Catalyzed P ‐Arylation of HP(= O)(R/OR) 2 Nucleophiles with (Hetero)Aryl Chlorides Enabled by DalPhos Ligation0Dinuclear Ni enabled reductive diarylation of dienes: Intramolecular comproportionation as the key mechanistic driver1Copper-Catalyzed Radical Halocyclization of N -4-Pentenamides: Synthesis of Chloro- and Bromo-Substituted γ-Lactams3On the reactions of (hetero)aryl and vinyl triflates with [Ni(COD)(dppf)]0Nickel-Catalyzed Aryl Borylations: Opportunities and Challenges for Innovation13A New Metal‐Ester Bonding Motif for the Synthesis of Hybrid Molecular Catalysts on Metal Oxide Supports Leads to Tunable Reactivity0A New Metal‐Ester Bonding Motif for the Synthesis of Hybrid Molecular Catalysts on Metal Oxide Supports Leads to Tunable Reactivity0Combining High‐Throughput Experimentation and Automated Flow for Bayesian Optimization of a Metallaphotoredox Reaction1Combining High‐Throughput Experimentation and Automated Flow for Bayesian Optimization of a Metallaphotoredox Reaction2Well‐Defined Nickel Precatalysts: Form, Function, and Application01915 Ni-catalyzed cross-coupling reactions0Air-Stable Nickel(0) Complexes with Room-Temperature Photoluminescence0

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  1. Inhibition of (dppf)nickel-catalysed Suzuki–Miyaura cross-coupling reactions by α-halo-N-heterocycles

    Chemical Science · 2021-01-01

    Alasdair K. Cooper, Megan Greaves, William Donohoe, Paul M. Burton, Thomas O. Ronson, Alan Robert Kennedy, David J. Nelson

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  2. Selective synthesis of fluorinated biaryls by [MCl 2 (PhPEWO-F)] (M = Ni, Pd) catalysed Negishi cross-coupling

    Chemical Communications · 2021-01-01

    Jaime Ponce‐de‐León, Pablo Espinet

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  3. The Effect of Added Ligands on the Reactions of [Ni(COD)(dppf)] with Alkyl Halides: Halide Abstraction can be Reversible

    ChemRxiv · 2021-05-06

    Megan Greaves, Thomas O. Ronson, Feliu Maseras, David J. Nelson

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  4. The Effect of Added Ligands on the Reactions of [Ni(COD)(dppf)] with Alkyl Halides: Halide Abstraction May Be Reversible

    Organometallics · 2021-06-16

    Megan Greaves, Thomas O. Ronson, Feliu Maseras, David J. Nelson

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  5. Lewis Acid‐Promoted Oxidative Addition at a [Ni 0 (diphosphine) 2 ] Complex: The Critical Role of a Secondary Coordination Sphere

    Chemistry - A European Journal · 2021-09-22

    Joseph A. Zurakowski, Brady J. H. Austen, Maeve C. Dufour, Denis M. Spasyuk, David J. Nelson, Marcus W. Drover

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  6. Stereoconvergent and -divergent Synthesis of Tetrasubstituted Alkenes by Nickel-Catalyzed Cross-Couplings

    Journal of the American Chemical Society · 2021-11-04

    Daniel Zell, Cian Kingston, Janis Jermaks, Sleight R. Smith, Natalie Seeger, Jana Wassmer, Lauren E. Sirois, Chong Han, Haiming Zhang, Matthew S. Sigman, Francis Gosselin

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  7. A guide to secondary coordination sphere editing

    Chemical Society Reviews · 2022-01-01

    Marcus W. Drover

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  8. Mechanistic views and computational studies on transition-metal-catalyzed reductive coupling reactions

    Chemical Society Reviews · 2022-01-01

    Abing Duan, Fengjiao Xiao, Yu Lan, Linbin Niu

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  9. Ni-Catalysed intramolecular reductive aminocarbonylation of 2-haloaryl-tethered nitroarenes for the synthesis of dibenzazepine-based heterocycles

    Organic Chemistry Frontiers · 2022-01-01

    Zhe Chuan Feng, Jun‐An Ma, Chi Wai Cheung

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  10. Nickel(Ii) Phosphine-Catalysed Hydrodehalogenation of Aryl Halides Under Mild Ambient Conditions

    SSRN Electronic Journal · 2022-01-01

    Wai Yip Fan, Sebastian Jun Kai Guek, Li Ji, Hwee‐Ling Koh, James Wen Liang Loke

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  11. Nickel and Palladium Catalysis: Stronger Demand than Ever

    ACS Catalysis · 2022-01-05

    Victor M. Chernyshev, Valentine P. Ananikov

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  12. Mapping Dual‐Base‐Enabled Nickel‐Catalyzed Aryl Amidations: Application in the Synthesis of 4‐Quinolones

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    Ryan T. McGuire, Travis Lundrigan, Joshua W. M. MacMillan, Katherine N. Robertson, Arun A. Yadav, Mark Stradiotto

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  13. Mapping Dual‐Base‐Enabled Nickel‐Catalyzed Aryl Amidations: Application in the Synthesis of 4‐Quinolones

    Angewandte Chemie International Edition · 2022-01-27

    Ryan T. McGuire, Travis Lundrigan, Joshua W. M. MacMillan, Katherine N. Robertson, Arun A. Yadav, Mark Stradiotto

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  14. Nickel (0) Complexes as Promising Chemosensors for Detecting the “Cork Taint” in Wine

    European Journal of Inorganic Chemistry · 2022-02-09

    Caterina Damiano, Daniela Intrieri, Paolo Sonzini, Silvia Rizzato, Corrado Di Natale, Roberto Paolesse, Emma Gallo

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  15. Exterior decorating: Lewis acid secondary coordination spheres for cooperative reactivity

    Trends in Chemistry · 2022-02-20

    Joseph A. Zurakowski, Brady J. H. Austen, Marcus W. Drover

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  16. Photoredox Activation of Inert Alkyl Chlorides for the Reductive Cross‐Coupling with Aromatic Alkenes

    Angewandte Chemie International Edition · 2022-03-14

    Jordi Aragón, Suyun Sun, David Pascual, Sebastian Jaworski, Julio Lloret‐Fillol

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  17. Photoredox Activation of Inert Alkyl Chlorides for the Reductive Cross‐Coupling with Aromatic Alkenes

    Angewandte Chemie · 2022-03-14

    Jordi Aragón, Suyun Sun, David Pascual, Sebastian Jaworski, Julio Lloret‐Fillol

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  18. Nickel(II) phosphine-catalysed hydrodehalogenation of aryl halides under mild ambient conditions

    Molecular Catalysis · 2022-04-25

    Sebastian Jun Kai Guek, Li Ji, James Wen Liang Loke, Hwee‐Ling Koh, Wai Yip Fan

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  19. Ligand-Based Control of Nickel Catalysts: Switching Chemoselectivity from One-Electron to Two-Electron Pathways in Competing Reactions of 4-Halotetrahydropyrans

    Organic Letters · 2022-05-13

    Taylor A. Thane, Elizabeth R. Jarvo

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  20. Selective Nickel-Catalyzed Hydrodefluorination of Amides Using Sodium Borohydride

    The Journal of Organic Chemistry · 2022-07-12

    Bernard F. Parker, Naoto Chatani

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  21. Three-Electron Nickel(I)/Nickel(0) Half-Bond

    Inorganic Chemistry · 2022-09-30

    Neil A. Dodd, Yu Cao, John Bacsa, Eric C. Towles, Thomas G. Gray, Joseph P. Sadighi

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  22. Structure–Reactivity Relationships of Buchwald-Type Phosphines in Nickel-Catalyzed Cross-Couplings

    Journal of the American Chemical Society · 2022-10-17

    Samuel H. Newman-Stonebraker, Jason Y. Wang, Philip D. Jeffrey, Abigail G. Doyle

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  23. 1,1′‐Bis(diphenylphosphino)ferrocene

    Encyclopedia of Reagents for Organic Synthesis · 2022-10-20

    William J. Kelly, Yamina Belabassi, Sonia Gouault‐Bironneau, Jean‐Luc Montchamp, Megan Greaves

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  24. Nickel Catalysis via S H 2 Homolytic Substitution: The Double Decarboxylative Cross-Coupling of Aliphatic Acids

    Journal of the American Chemical Society · 2022-11-14

    Artem V. Tsymbal, Lorenzo Delarue Bizzini, David W. C. MacMillan

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  25. A Decarboxylative Cross-Coupling Platform To Access 2-Heteroaryl Azetidines: Building Blocks with Application in Medicinal Chemistry

    Organic Letters · 2022-12-07

    James T. Brewster, Samuel D. Randall, John P. Kowalski, Cole L. Cruz, Richard N. Shoemaker, Eugene Tarlton, Ronald J. Hinklin

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  26. Theoretical investigation of mechanism on nickel-catalyzed electrochemical cross-coupling of aryl bromides and arylamines

    Catalysis Science & Technology · 2022-12-27

    Xin Wang, Yueyue Ma, Jinxing Ye, Zhen Liu, Ruihua Cheng

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  27. Photocatalytic C–O Coupling Enzymes That Operate via Intramolecular Electron Transfer

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  28. Nickel Complexes of Allyl and Vinyldiphenylphosphine

    ChemRxiv · 2023-03-16

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  29. Interrogating the Mechanistic Features of Ni(I)-Mediated Aryl Iodide Oxidative Addition Using Electroanalytical and Statistical Modeling Techniques

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  30. Nickel Complexes of Allyl and Vinyldiphenylphosphine

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  31. A Simple Protocol for the C−N Cross‐Coupling of Aryl Chlorides with Amines Applying Ni/NHC Catalysis

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  32. Stability and C–H Bond Activation Reactions of Palladium(I) and Platinum(I) Metalloradicals: Carbon-to-Metal H-Atom Transfer and an Organometallic Radical Rebound Mechanism

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    Tobias Krämer, Matthew R. Gyton, Itxaso Bustos, Matthew J. G. Sinclair, Sze‐yin Tan, Christopher J. Wedge, Stuart A. Macgregor, Adrian B. Chaplin

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  33. Electrochemical Nickel-Catalyzed C(sp3)–C(sp3) Cross-Coupling of Alkyl Halides with Alkyl Tosylates

    Journal of the American Chemical Society · 2023-07-26

    Malek Y. S. Ibrahim, Graham R. Cumming, Raquel González de Vega, Pablo García‐Losada, Óscar de Frutos, Christian Oliver Kappe, David Cantillo

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  34. Recent advances in catalytic and electrocatalytic applications of half‐sandwich nickel(0/II) N–heterocyclic carbene complexes

    Applied Organometallic Chemistry · 2023-09-04

    Srinivasa Budagumpi, K.N. Brinda, Rangappa Sangappa Keri, Nagaraju Doddahalli Hanumantharayudu, Monica Vijayakumar, Periasamy Viswanathamurthi

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  35. Branched-Selective Cross-Electrophile Coupling of 2-Alkyl Aziridines and (Hetero)aryl Iodides Using Ti/Ni Catalysis

    Journal of the American Chemical Society · 2023-10-27

    Wendy L. Williams, Neyci Gutierrez Valencia, Abigail G. Doyle

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  36. A tale of two metals: The Mizoroki-Heck reaction as a guide to compare the chemical characters of nickel and palladium in catalysis

    Advances in organometallic chemistry · 2024-01-01

    Tomás G. Santiago, Pilar Palma, Juan Cámpora

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  37. Ligand redistribution hinders preparation of a nickel(II)-hydroxo

    Canadian Journal of Chemistry · 2024-01-19

    Shagana Kukendran, John S. Lee, Paul D. Boyle, Johanna M. Blacquiere

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  38. Computational Methods Enable the Prediction of Improved Catalysts for Nickel-Catalyzed Cross-Electrophile Coupling

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  39. Nickel-Catalyzed Arylation/Lactonization Cascade Reactions for the Synthesis of Bicyclo[3.2.1]lactones

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  40. Engaging Alkenes in Metallaphotoredox: A Triple Catalytic, Radical Sorting Approach to Olefin-Alcohol Cross-Coupling

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  41. Chemo- and Regioselective Nickel-Catalyzed Reductive 1,4-Alkylarylation of 1,3-Enynes through an L2NiAr Intermediate

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  42. Boryl radical-mediated halogen-atom transfer enables arylation of alkyl halides with electrophilic and nucleophilic coupling partners

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  43. Computational Study of the Ir-Catalyzed Formation of Allyl Carbamates from CO2

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  44. A Strategy for the Formal C−N Cross‐Coupling of Tertiary Amines

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  45. A Strategy for the Formal C−N Cross‐Coupling of Tertiary Amines

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  46. Bis(benzimidazolin-2-ylidenes): Exploring the Impact of Ligand Properties in the Nickel-Catalyzed Suzuki–Miyaura Coupling

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    Claudia S. Zhang, Shreyas Rajesh, Abigail L. Moffett, Timothy H. Chen, Colin D. McMillen, Kerry‐Ann Green

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  47. A decarbonylative approach to alkylnickel intermediates and C(sp 3 )-C(sp 3 ) bond formation

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  48. Mapping Electrophile Chemoselectivity in DalPhos/Nickel N‐Arylation Catalysis: The Unusual Influence of Remote Sterics

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  49. Varying Lewis Acidity, Covalency, and Halide Mobility to Govern Oxidative Addition Reactivity of Ni–Group 13 Bimetallic Complexes

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  50. Decarboxylative Cross-Coupling Enabled by Fe and Ni Metallaphotoredox Catalysis

    Journal of the American Chemical Society · 2024-10-18

    Reem Nsouli, Sneha Nayak, Venkadesh Balakrishnan, Jung-Ying Lin, Karen Benjamin, Hannah G. Ford, Andrew V. Tran, Ilia A. Guzei, John Bacsa, Nicholas R. Armada, Fedor Zenov, Daniel J. Weix, Laura K. G. Ackerman

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