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RESEARCH PAPER · Inorganic Chemistry · 2008

Halide Ligands—More Than Just σ-Donors? A Structural and Spectroscopic Study of Homologous Organonickel Complexes

Axel Klein, André Kaiser, Wolfram Wielandt, Ferdinand Belaj, Eric Wendel, H. Bertagnolli, Stanislav Záliš

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Halide Ligands—More Than Just σ-Donors? A Structural and Spectroscopic Study of Homologous Organonickel ComplexesOriginalTowards X‐Ray Absorption Spectroscopy in Real Time9Mono‐ and Binuclear Arylnickel Complexes of the α‐Diimine Bridging Ligand 2,2′‐Bipyrimidine (bpym)9Synthesis of N-alkyl and N-aryl isoquinolones and derivatives via Pd-catalysed C–H activation and cyclization reactions62Binuclear Arylnickel Complexes with Bridging Bis(arylimino)‐1,4‐pyrazine Ligands7Replacing Conventional Carbon Nucleophiles with Electrophiles: Nickel-Catalyzed Reductive Alkylation of Aryl Bromides and Chlorides420Electrochemical Synthesis and Properties of Organonickel σ-Complexes42The cyclometalated nickel complex [(Phbpy)NiBr] (Phbpy− = 2,2′-bipyridine-6-phen-2-yl) – Synthesis, spectroscopic and electrochemical studies28Nickel Bromide Bipyridine5Switching on elusive organometallic mechanisms with photoredox catalysis630First example of organonickel complex bearing three cyclic substituents in the σ-bonded aromatic ring: bromo[(2,2’ -bipyridine)-2,4,6-tricyclohexylphenylnickel]18Photochemical Nickel-Catalyzed C–H Arylation: Synthetic Scope and Mechanistic Investigations518Synthesis, Structure and Reactivity of Cyclometalated Nickel(II) Complexes: A Review and Perspective17Unsymmetrical N-Aryl-1-(pyridin-2-yl)methanimine Ligands in Organonickel(II) Complexes: More Than a Blend of 2,2′-Bipyridine and N,N-Diaryl-α-diimines?14Electrochemical methods for synthesis of organoelement compounds and functional materials20The merger of transition metal and photocatalysis2226Trifluoromethylation of a Well‐Defined Square‐Planar Aryl‐NiII Complex involving NiIII/CF3. and NiIV−CF3 Intermediate Species27Nickel-catalyzed intermolecular carboiodination of alkynes with aryl iodides41Long-Lived Charge-Transfer States of Nickel(II) Aryl Halide Complexes Facilitate Bimolecular Photoinduced Electron Transfer296Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation218Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides237Stereoselective Preparation of α- C -Vinyl/Aryl Glycosides via Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Vinyl and Aryl Halides127Nickel-catalyzed reductive coupling of glucosyl halides with aryl/vinyl halides enabling β-selective preparation of C-aryl/vinyl glucosides70Ni-Catalyzed Reductive Dicarbofunctionalization of Nonactivated Alkenes: Scope and Mechanistic Insights243Photo‐Assisted Nickel‐Catalyzed Cross‐Coupling Processes33 d-d Excited States of Ni(II) Complexes Relevant to Photoredox Catalysis: Spectroscopic Identification and Mechanistic Implications296Cyclometalated Ni(II) Complexes [Ni(N∧C∧N)X] of the Tridentate 2,6-di(2-pyridyl)phen-ide Ligand34Ni-Catalyzed Reductive and Merged Photocatalytic Cross-Coupling Reactions toward sp3/sp2-Functionalized Isoquinolones: Creating Diversity at C-6 and C-7 to Address Bioactive Analogues14Photoactive Nickel Complexes in Cross‐Coupling Catalysis106The impact of ligands on the synthesis and application of metal halide perovskite nanocrystals139Diaryl Ether Formation Merging Photoredox and Nickel Catalysis40Role of the X Coligands in Cyclometalated [Ni(Phbpy)X] Complexes (HPhbpy = 6-Phenyl-2,2′-bipyridine)17Monovalent Nickel-Mediated Radical Formation: A Concerted Halogen-Atom Dissociation Pathway Determined by Electroanalytical Studies124A Pivotal Role of Chloride Ion on Nickel-Catalyzed Enantioselective Reductive Cross-Coupling to Perfluoroalkylated Boronate Esters45Asymmetrically Difunctionalized 1,1′‐Ferrocenyl Metalloligands and Their Transition Metal Complexes9Nickel-Carbon σ-Bonded Complexes2Modular terpene synthesis enabled by mild electrochemical couplings158Direct Synthesis of α‐Aryl‐α‐Trifluoromethyl Alcohols via Nickel Catalyzed Cross‐Electrophile Coupling51Direct Synthesis of α‐Aryl‐α‐Trifluoromethyl Alcohols via Nickel Catalyzed Cross‐Electrophile Coupling4Photoinduced Nickel‐Catalyzed Carbon–Heteroatom Coupling**39Triplet Emitting C^N^C Cyclometalated Dibenzo[c,h]Acridine Pt(II) Complexes4SYNTHESIS, STRUCTURE, AND PROPERTIES OF THE ORGANONICKEL σ-COMPLEX [NiBr(Pmp)(bpy)], WHERE Pmp IS 2,3,4,5,6- PENTAMETHYLPHENYL, bpy IS 2,2′-BIPYRIDINE3The Role of Anionic Ligands on Photoreactivity in Mo(VI) Dioxo Complexes of the Form MoO2X2(NN)**7Nickel-Catalyzed Enantioselective Reductive Arylation and Heteroarylation of Aldimines via an Elementary 1,4-Addition54Effect of 6,6′-Substituents on Bipyridine-Ligated Ni Catalysts for Cross-Electrophile Coupling27Multiconfigurational Electronic Structure of Nickel Cross-Coupling Catalysts Revealed by X-ray Absorption Spectroscopy9A Unified Approach to Chiral α-Aryl Ketones and Aldehydes via Ni-Catalyzed Asymmetric Reductive Cross-Coupling12Preparation of Chiral α-Aryl Ketones and Aldehydes via Ni-Catalyzed Asymmetric Cross-Electrophile Coupling1Thermal Bimolecular Homodimerization Initiates Nickel(I) Catalysis from 2,6-Aryl-Unsubstituted Bipyridyl Nickel(II) Oxidative Addition Complexes0

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  1. Towards X‐Ray Absorption Spectroscopy in Real Time

    ChemPhysChem · 2009-07-13

    Matthias Bauer, H. Bertagnolli

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  2. Mono‐ and Binuclear Arylnickel Complexes of the α‐Diimine Bridging Ligand 2,2′‐Bipyrimidine (bpym)

    European Journal of Inorganic Chemistry · 2010-01-12

    Axel Klein, A.-K. Schmieder, Natascha Hurkes, Claudia Hamacher, Andreas O. Schüren, Martin P. Feth, H. Bertagnolli

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  3. Synthesis of N-alkyl and N-aryl isoquinolones and derivatives via Pd-catalysed C–H activation and cyclization reactions

    Organic & Biomolecular Chemistry · 2012-01-01

    Nana Zhang, Binyao Li, Hongban Zhong, Jianhui Huang

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  4. Binuclear Arylnickel Complexes with Bridging Bis(arylimino)‐1,4‐pyrazine Ligands

    European Journal of Inorganic Chemistry · 2012-03-30

    Axel Klein, Christian Biewer, Claudia Hamacher, Natascha Hurkes, Jessica Perez Outeiral, Erik Mora Paniagua, A.-K. Schmieder, Andreas O. Schüren, Prabhakara Rao Burma, James T. Ciszewski, David A. Vicic

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  5. Replacing Conventional Carbon Nucleophiles with Electrophiles: Nickel-Catalyzed Reductive Alkylation of Aryl Bromides and Chlorides

    Journal of the American Chemical Society · 2012-03-30

    Daniel A. Everson, Brittany A. Jones, Daniel J. Weix

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  6. Electrochemical Synthesis and Properties of Organonickel σ-Complexes

    Organometallics · 2014-05-02

    Dmitry G. Yakhvarov, Aliya F. Khusnuriyalova, Oleg Gerol'dovich Sinyashin

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  7. The cyclometalated nickel complex [(Phbpy)NiBr] (Phbpy− = 2,2′-bipyridine-6-phen-2-yl) – Synthesis, spectroscopic and electrochemical studies

    Journal of Organometallic Chemistry · 2014-10-15

    Axel Klein, Benjamin Rausch, André Kaiser, Nicolas Vogt, Alexander Krest

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  8. Nickel Bromide Bipyridine

    Encyclopedia of Reagents for Organic Synthesis · 2014-10-20

    Muriel Durandetti, Jacques F. Maddaluno

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  9. Switching on elusive organometallic mechanisms with photoredox catalysis

    Nature · 2015-08-01

    Jack A. Terrett, James D. Cuthbertson, Valerie W. Shurtleff, David W. C. MacMillan

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  10. First example of organonickel complex bearing three cyclic substituents in the σ-bonded aromatic ring: bromo[(2,2’ -bipyridine)-2,4,6-tricyclohexylphenylnickel]

    Mendeleev Communications · 2016-03-01

    I. F. Sakhapov, Zufar N. Gafurov, Vasily M. Babaev, Il'dar Kh. Rizvanov, Alexey B. Dobrynin, Dmitry B. Krivolapov, Khasan Rafaelevich Khayarov, Oleg Gerol'dovich Sinyashin, Dmitry G. Yakhvarov

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  11. Photochemical Nickel-Catalyzed C–H Arylation: Synthetic Scope and Mechanistic Investigations

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    Drew R. Heitz, John C. Tellis, Gary Alan Molander

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  12. Synthesis, Structure and Reactivity of Cyclometalated Nickel(II) Complexes: A Review and Perspective

    Proceedings of the National Academy of Sciences India Section A Physical Sciences · 2016-09-23

    Axel Klein, Aaron Sandleben, Nicolas Vogt

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  13. Unsymmetrical N-Aryl-1-(pyridin-2-yl)methanimine Ligands in Organonickel(II) Complexes: More Than a Blend of 2,2′-Bipyridine and N,N-Diaryl-α-diimines?

    Inorganic Chemistry · 2016-12-01

    Christian Biewer, Claudia Hamacher, André Kaiser, Nicolas Vogt, Aaron Sandleben, Mason T. Chin, Siqi Yu, David A. Vicic, Axel Klein

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  14. Electrochemical methods for synthesis of organoelement compounds and functional materials

    Pure and Applied Chemistry · 2017-04-19

    Zufar N. Gafurov, Oleg Gerol'dovich Sinyashin, Dmitry G. Yakhvarov

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  15. The merger of transition metal and photocatalysis

    Nature Reviews Chemistry · 2017-07-05

    Jack Twilton, Chi “Chip” Le, Patricia Zhang Musacchio, Megan H. Shaw, Ryan W. Evans, David W. C. MacMillan

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  16. Trifluoromethylation of a Well‐Defined Square‐Planar Aryl‐NiII Complex involving NiIII/CF3. and NiIV−CF3 Intermediate Species

    Chemistry - A European Journal · 2017-07-07

    Mireia Rovira, Steven Roldán‐Gómez, Vlad Martin‐Diaconescu, Christopher J. Whiteoak, Josep Maria Luis, Xavi Ribas

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  17. Nickel-catalyzed intermolecular carboiodination of alkynes with aryl iodides

    Chemical Communications · 2018-01-01

    Toshifumi Takahashi, Daiki Kuroda, Toru Kuwano, Yūji Yoshida, Takuya Kurahashi, Seijiro Matsubara

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  18. Long-Lived Charge-Transfer States of Nickel(II) Aryl Halide Complexes Facilitate Bimolecular Photoinduced Electron Transfer

    Journal of the American Chemical Society · 2018-02-05

    Benjamin J. Shields, Bryan J. Kudisch, Gregory D. Scholes, Abigail G. Doyle

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  19. Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation

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  20. Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides

    Journal of the American Chemical Society · 2018-10-08

    Xuan Wang, Xuan Wang, Guobin Ma, Yu Peng, Chloe E. Pitsch, Brenda J. Moll, Thu D. Ly, Xiaotai Wang, Xiaotai Wang, Hegui Gong

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  21. Stereoselective Preparation of α- C -Vinyl/Aryl Glycosides via Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Vinyl and Aryl Halides

    Organic Letters · 2018-12-10

    Jiandong Liu, Hegui Gong

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  22. Nickel-catalyzed reductive coupling of glucosyl halides with aryl/vinyl halides enabling β-selective preparation of C-aryl/vinyl glucosides

    Science China Chemistry · 2019-06-18

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

    Journal of the American Chemical Society · 2019-08-21

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  24. Photo‐Assisted Nickel‐Catalyzed Cross‐Coupling Processes

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  25. 3 d-d Excited States of Ni(II) Complexes Relevant to Photoredox Catalysis: Spectroscopic Identification and Mechanistic Implications

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  26. Cyclometalated Ni(II) Complexes [Ni(N∧C∧N)X] of the Tridentate 2,6-di(2-pyridyl)phen-ide Ligand

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  27. Ni-Catalyzed Reductive and Merged Photocatalytic Cross-Coupling Reactions toward sp3/sp2-Functionalized Isoquinolones: Creating Diversity at C-6 and C-7 to Address Bioactive Analogues

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  28. Photoactive Nickel Complexes in Cross‐Coupling Catalysis

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  29. The impact of ligands on the synthesis and application of metal halide perovskite nanocrystals

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  30. Diaryl Ether Formation Merging Photoredox and Nickel Catalysis

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  31. Role of the X Coligands in Cyclometalated [Ni(Phbpy)X] Complexes (HPhbpy = 6-Phenyl-2,2′-bipyridine)

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  32. Monovalent Nickel-Mediated Radical Formation: A Concerted Halogen-Atom Dissociation Pathway Determined by Electroanalytical Studies

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  33. A Pivotal Role of Chloride Ion on Nickel-Catalyzed Enantioselective Reductive Cross-Coupling to Perfluoroalkylated Boronate Esters

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  34. Asymmetrically Difunctionalized 1,1′‐Ferrocenyl Metalloligands and Their Transition Metal Complexes

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  36. Modular terpene synthesis enabled by mild electrochemical couplings

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  37. Direct Synthesis of α‐Aryl‐α‐Trifluoromethyl Alcohols via Nickel Catalyzed Cross‐Electrophile Coupling

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  38. Direct Synthesis of α‐Aryl‐α‐Trifluoromethyl Alcohols via Nickel Catalyzed Cross‐Electrophile Coupling

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  39. Photoinduced Nickel‐Catalyzed Carbon–Heteroatom Coupling**

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  41. SYNTHESIS, STRUCTURE, AND PROPERTIES OF THE ORGANONICKEL σ-COMPLEX [NiBr(Pmp)(bpy)], WHERE Pmp IS 2,3,4,5,6- PENTAMETHYLPHENYL, bpy IS 2,2′-BIPYRIDINE

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  42. The Role of Anionic Ligands on Photoreactivity in Mo(VI) Dioxo Complexes of the Form MoO2X2(NN)**

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  43. Nickel-Catalyzed Enantioselective Reductive Arylation and Heteroarylation of Aldimines via an Elementary 1,4-Addition

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  44. Effect of 6,6′-Substituents on Bipyridine-Ligated Ni Catalysts for Cross-Electrophile Coupling

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  46. A Unified Approach to Chiral α-Aryl Ketones and Aldehydes via Ni-Catalyzed Asymmetric Reductive Cross-Coupling

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  48. Thermal Bimolecular Homodimerization Initiates Nickel(I) Catalysis from 2,6-Aryl-Unsubstituted Bipyridyl Nickel(II) Oxidative Addition Complexes

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