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RESEARCH PAPER · Organometallics · 2019

Bis(dialkylphosphino)ferrocene-Ligated Nickel(II) Precatalysts for Suzuki–Miyaura Reactions of Aryl Carbonates

Emily L. Barth, Ryan M. Davis, Megan Mohadjer Beromi, Andrew G. Walden, David Balcells, Gary W. Brudvig, Amira H. Dardir, Nilay Hazari, Hannah M. C. Lant, Brandon Q. Mercado, Ian L. Peczak

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Bis(dialkylphosphino)ferrocene-Ligated Nickel(II) Precatalysts for Suzuki–Miyaura Reactions of Aryl CarbonatesOriginalThe Synthesis and Catalytic Activity of New Mixed NHC-Phosphite Nickel(0) Complexes29Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni( ii ) β-oxodithioester-dppe] + ; their use as a catalyst for Chan–Lam coupling12Suzuki-Miyaura coupling catalyzed by a Ni(II) PNP pincer complex: Scope and mechanistic insights18Unexpected Nickel Complex Speciation Unlocks Alternative Pathways for the Reactions of Alkyl Halides with dppf-Nickel(0)33Ligand Steric Effects of α-Diimine Nickel(II) and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling Reaction25Reactions of nickel(0) with organochlorides, organobromides, and organoiodides: mechanisms and structure/reactivity relationships80Biaryl Construction Based on Nickel-Catalyzed C–O Bond Activation62,2-difluorovinyl benzoates for diverse synthesis of gem-difluoroenol ethers by Ni-catalyzed cross-coupling reactions27Suzuki–Miyaura Csp2–Csp2 Cross-Couplings Employing Nickel(II) Pincer Precatalysts: Mechanistic Investigations7Synthesis, characterization, and oxidation electrochemistry of some novel 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones containing aryl and metallocenyl fragments7Late transition metal nanocomplexes: Applications for renewable energy conversion and storage34Advancing Base-Metal Catalysis: Development of a Screening Method for Nickel-Catalyzed Suzuki–Miyaura Reactions of Pharmaceutically Relevant Heterocycles43Characterization Methods for Paramagnetic Organometallic Complexes1Nickel-Catalyzed Kumada Vinylation of Enol Phosphates: A Comparative Mechanistic Study11Nickel-Carbon σ-Bonded Complexes2Robust Analytical Methods for Monitoring the Formation of a Chiral Oxazaborolidine Catalyst3Comproportionation and disproportionation in nickel and copper complexes86Nucleophilic Aromatic Substitution0Elucidating electron-transfer events in polypyridine nickel complexes for reductive coupling reactions112Phosphine Functionalized CpC Ligands and Their Metal Complexes2Comparison of Monophosphine and Bisphosphine Precatalysts for Ni-Catalyzed Suzuki–Miyaura Cross-Coupling: Understanding the Role of the Ligation State in Catalysis42Ni(I) complexes relevant to synthetic organic catalysis0Stereodivergent, Kinetically Controlled Isomerization of Terminal Alkenes via Nickel Catalysis38Stereodivergent, Kinetically Controlled Isomerization of Terminal Alkenes via Nickel Catalysis5Suzuki-Miyaura Cross-Coupling using convenient and accessible Nickelocene/Phosphine precatalyst2Bis(benzimidazolin-2-ylidenes): Exploring the Impact of Ligand Properties in the Nickel-Catalyzed Suzuki–Miyaura Coupling5Advances in accessing rare oxidation states of nickel for catalytic innovation15Discovery of Ni(I) Complexes for CO2 Insertion Enabled by a Machine Learning-Computational-Selection Sequence12Comparison of Alkyl-Bridged Bis(N-Heterocyclic Carbene) Nickel Precatalysts: Structure and Catalytic Activity in the Reductive Cleavage and Suzuki–Miyaura Reactions3Controlling the Redox Speciation of N,C,N–Bi Complexes Using the Anion Coordination Index0

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  1. The Synthesis and Catalytic Activity of New Mixed NHC-Phosphite Nickel(0) Complexes

    Organometallics · 2019-12-27

    Jeremy A. Duczynski, Alexandre N. Sobolev, Stephen A. Moggach, Reto Dorta, Scott G. Stewart

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  2. Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni( ii ) β-oxodithioester-dppe] + ; their use as a catalyst for Chan–Lam coupling

    New Journal of Chemistry · 2020-01-01

    Kavita Kumari, Saurabh Kumar, Krishna Nand Singh, Michael G. B. Drew, Nanhai Singh

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  3. Suzuki-Miyaura coupling catalyzed by a Ni(II) PNP pincer complex: Scope and mechanistic insights

    Inorganica Chimica Acta · 2020-01-23

    Justin Madera, Megan Slattery, Hadi D. Arman, Zachary J. Tonzetich

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  4. Unexpected Nickel Complex Speciation Unlocks Alternative Pathways for the Reactions of Alkyl Halides with dppf-Nickel(0)

    ACS Catalysis · 2020-08-21

    Megan Greaves, Thomas O. Ronson, Guy C. Lloyd‐Jones, Feliu Maseras, Stephen A. Sproules, David J. Nelson

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  5. Ligand Steric Effects of α-Diimine Nickel(II) and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling Reaction

    ACS Omega · 2020-09-10

    Md Muktadir Talukder, John Michael O. Cue, Justin T. Miller, Prabhath L. Gamage, Amina Aslam, Gregory T. McCandless, Michael C. Biewer, Mihaela C. Stefan

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

    Catalysis Science & Technology · 2021-01-01

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

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  7. Biaryl Construction Based on Nickel-Catalyzed C–O Bond Activation

    Synlett · 2021-01-11

    Feng Liu, Haiyan Diao, Zhang‐Jie Shi

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  8. 2,2-difluorovinyl benzoates for diverse synthesis of gem-difluoroenol ethers by Ni-catalyzed cross-coupling reactions

    Nature Communications · 2021-01-18

    Bingnan Du, Chun‐Ming Chan, Pui‐Yiu Lee, Leong‐Hung Cheung, Xin Hua Xu, Zhenyang Lin, Wing‐Yiu Yu

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  9. Suzuki–Miyaura Csp2–Csp2 Cross-Couplings Employing Nickel(II) Pincer Precatalysts: Mechanistic Investigations

    Organometallics · 2021-04-14

    Curtis C. Ho, Angus Olding, Rebecca O. Fuller, Allan J. Canty, Nigel T. Lucas, Alex C. Bissember

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  10. Synthesis, characterization, and oxidation electrochemistry of some novel 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones containing aryl and metallocenyl fragments

    Journal of Organometallic Chemistry · 2021-04-16

    Jessica J. Sánchez García, Rene S. Joo-Cisneros, David García-Bassoco, Marcos Flores-Álamo, José Manuel Méndez Stivalet, Jesús Garcı́a-Valdés, Elena Ivanovna Klimova

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  11. Late transition metal nanocomplexes: Applications for renewable energy conversion and storage

    Renewable and Sustainable Energy Reviews · 2021-04-20

    Nurul Akmal Che Lah

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  12. Advancing Base-Metal Catalysis: Development of a Screening Method for Nickel-Catalyzed Suzuki–Miyaura Reactions of Pharmaceutically Relevant Heterocycles

    Organic Process Research & Development · 2021-07-28

    Matthew J. Goldfogel, Xuelei Guo, Jeishla L. M. Matos, John A. Gurak, Matthew V. Joannou, William B. Moffat, Eric M. Simmons, Steven R. Wisniewski

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  13. Characterization Methods for Paramagnetic Organometallic Complexes

    Elsevier eBooks · 2021-09-27

    Aleksa Radović, Shilpa Bhatia, Michael L. Neidig

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  14. Nickel-Catalyzed Kumada Vinylation of Enol Phosphates: A Comparative Mechanistic Study

    ACS Catalysis · 2021-12-01

    Philippe‐Alexandre Poisson, Gaël Tran, Céline Besnard, Clément Mazet

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  15. Nickel-Carbon σ-Bonded Complexes

    Elsevier eBooks · 2022-01-01

    Clifton L. Wagner, Tianning Diao

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  16. Robust Analytical Methods for Monitoring the Formation of a Chiral Oxazaborolidine Catalyst

    Organic Process Research & Development · 2022-03-16

    Sloan Ayers, Gregory L. Beutner, Wei Ding, Carolyn S. Higman, Charles Pathirana, Robert G. Wethman

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  17. Comproportionation and disproportionation in nickel and copper complexes

    Chemical Society Reviews · 2023-01-01

    Craig S. Day, Rubén Martı́n

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  18. Nucleophilic Aromatic Substitution

    Organic Reaction Mechanisms/Organic reaction mechanisms · 2023-01-20

    M. R. Crampton

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

    Nature Catalysis · 2023-03-09

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

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  20. Phosphine Functionalized CpC Ligands and Their Metal Complexes

    Chemistry · 2023-04-18

    Florian Nährig, Yu Sun, Werner Richard Thiel

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  21. Comparison of Monophosphine and Bisphosphine Precatalysts for Ni-Catalyzed Suzuki–Miyaura Cross-Coupling: Understanding the Role of the Ligation State in Catalysis

    ACS Catalysis · 2023-05-30

    Julia E. Borowski, Samuel H. Newman-Stonebraker, Abigail G. Doyle

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  22. Ni(I) complexes relevant to synthetic organic catalysis

    Advances in organometallic chemistry · 2024-01-01

    Dale J. Wilger, Lydia P. Moore, Molly M. Lockart

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  23. Stereodivergent, Kinetically Controlled Isomerization of Terminal Alkenes via Nickel Catalysis

    Angewandte Chemie International Edition · 2024-03-18

    Camille Rubel, Anne K. Ravn, Hang Chi Ho, Shenghua Yang, Zi‐Qi Li, Keary M. Engle, Julien C. Vantourout

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  24. Stereodivergent, Kinetically Controlled Isomerization of Terminal Alkenes via Nickel Catalysis

    Angewandte Chemie · 2024-03-18

    Camille Rubel, Anne K. Ravn, Hang Chi Ho, Shenghua Yang, Zi‐Qi Li, Keary M. Engle, Julien C. Vantourout

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  25. Suzuki-Miyaura Cross-Coupling using convenient and accessible Nickelocene/Phosphine precatalyst

    Journal of Catalysis · 2024-07-02

    Łukasz Banach, Jakub Robaszkiewicz, Piotr Pawluć

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

    Organometallics · 2024-09-12

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

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  27. Advances in accessing rare oxidation states of nickel for catalytic innovation

    Chemical Communications · 2025-01-01

    Aankhi Khamrai, Sudipta Ghosh, Venkataraman Ganesh

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  28. Discovery of Ni(I) Complexes for CO2 Insertion Enabled by a Machine Learning-Computational-Selection Sequence

    Journal of the American Chemical Society · 2025-07-18

    Julian A. Hueffel, Mathilde Rigoulet, Sebastian Wellig, Theresa Sperger, Jas S. Ward, Kari T. Rissanen, Franziska Schoenebeck

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  29. Comparison of Alkyl-Bridged Bis(N-Heterocyclic Carbene) Nickel Precatalysts: Structure and Catalytic Activity in the Reductive Cleavage and Suzuki–Miyaura Reactions

    ACS Omega · 2025-11-17

    Claudia S. Zhang, Eleanor C. Beams, Abigail L. Moffett, Chuyi Luo, Colin D. McMillen, A. Chianese, Kerry‐Ann Green

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  30. Controlling the Redox Speciation of N,C,N–Bi Complexes Using the Anion Coordination Index

    Organometallics · 2026-03-24

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