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RESEARCH PAPER · Chemical Society Reviews · 2016

Dinuclear Pd I complexes with bridging allyl and related ligands

Nilay Hazari, Damian P. Hruszkewycz

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Dinuclear Pd I complexes with bridging allyl and related ligandsOriginalChemInform Abstract: Dinuclear PdI Complexes with Bridging Allyl and Related Ligands0Ligand and base additive effects on the reversibility of nucleophilic addition in palladium-catalyzed allylic aminations monitored by nucleophile crossover12Synthetic and Mechanistic Interrogation of Pd/Isocyanide-Catalyzed Cross-Coupling: π-Acidic Ligands Enable Self-Aggregating Monoligated Pd(0) Intermediates30Detection of Palladium(I) in Aerobic Oxidation Catalysis59Detection of Palladium(I) in Aerobic Oxidation Catalysis16Mechanism of the Suzuki–Miyaura Cross-Coupling Reaction Mediated by [Pd(NHC)(allyl)Cl] Precatalysts82Hydrogenation of nitroarenes catalyzed by a dipalladium complex7Insights into the Catalytic Activity of [Pd(NHC)(cin)Cl] (NHC=IPr, IPrCl, IPrBr) Complexes in the Suzuki–Miyaura Reaction40Mechanistic Basis for Efficient, Site-Selective, Aerobic Catalytic Turnover in Pd-Catalyzed C–H Imidoylation of Heterocycle-Containing Molecules29Carbon Dioxide Insertion into Group 9 and 10 Metal–Element σ Bonds98Buchwald–Hartwig amination using Pd( i ) dimer precatalysts supported by biaryl phosphine ligands25Dinuclear Nickel(I) and Palladium(I) Complexes for Highly Active Transformations of Organic Compounds57Designing Pd and Ni Catalysts for Cross-Coupling Reactions by Minimizing Off-Cycle Species98Mechanistic Study of Suzuki–Miyaura Cross‐Coupling Reactions of Amides Mediated by [Pd(NHC)(allyl)Cl] Precatalysts99Palladium-Catalyzed Aerobic Homocoupling of Alkynes: Full Mechanistic Characterization of a More Complex Oxidase-Type Behavior43C(sp3)–C(sp3) Coupling with a Pd(II) Complex Bearing a Structurally Responsive Ligand7Operando Spectroscopic and Kinetic Characterization of Aerobic Allylic C–H Acetoxylation Catalyzed by Pd(OAc)2/4,5-Diazafluoren-9-one40Development of Palladium Precatalysts that Efficiently Generate LPd(0) Active Species112Ligand‐Controlled C−O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights16Bonding and electronic structures in dinuclear (X)[(Ind)M2L2] complexes (M = Ni, Pd, L = CO, PEt3, X = Cl, Allyl, Ind = indenyl, Cp = cyclopentadienyl): analogy between four-electron donor ligands15Recent advances of dinuclear nickel- and palladium-complexes in homogeneous catalysis55Catalysis with Palladium(I) Dimers112Catalysis with Palladium(I) Dimers16C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd( i )–Pd( ii ) catalysis vs. Pd( ii ) catalysis66The Multifaceted Palladium Chemistry of 2,2′-Diphosphinotolanes12Isolation and Catalytic Reactivity of Mononuclear Palladium(I) Complexes0Glucopyranoside-Functionalized NHCs-Pd(II)-PEPPSI Complexes: Anomeric Isomerism Controlled and Catalytic Activity in Aqueous Suzuki Reaction11In Situ Formation of Cationic π-Allylpalladium Precatalysts in Alcoholic Solvents: Application to C–N Bond Formation18Cationic palladium( ii )-indenyl complexes bearing phosphines as ancillary ligands: synthesis, and study of indenyl amination and anticancer activity15Changes in ligand coordination mode induce bimetallic C–C coupling pathways6Monovalent Group 10 Organometallic Complexes1Palladium-catalyzed Lewis acid-regulated cascade annulation of alkynes with unactivated alkenes to access diverse α-methylene-γ-lactones11C−I Selective Sonogashira and Heck Coupling Reactions Catalyzed by Aromatic Triangular Tri‐palladium10Carbon–Carbon Bond Coupling of Vinyl Molecules with an Allenyl Ligand at a Diruthenium Complex18METAL-ORGANIC FRAMEWORKS IN RUSSIA: FROM THE SYNTHESIS AND STRUCTURE TO FUNCTIONAL PROPERTIES AND MATERIALS92Palladium-Catalyzed Three-Component Selective Aminoallylation of Diazo Compounds23Emerging Trends in Cross-Coupling: Twelve-Electron-Based L 1 Pd(0) Catalysts, Their Mechanism of Action, and Selected Applications179Isolation and Characterization of Heteroleptic Mononuclear Palladium(I) Complexes32Open cell foam materials as Pd reservoirs for Suzuki–Miyaura coupling catalysis at ppb level4Stability and C–H Bond Activation Reactions of Palladium(I) and Platinum(I) Metalloradicals: Carbon-to-Metal H-Atom Transfer and an Organometallic Radical Rebound Mechanism29Heteroaryl–Heteroaryl Suzuki–Miyaura Cross-Coupling Enabled by Large-but-Flexible Dibenzobarrelene-Derived Pd-NHC Precatalysts14Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics10Cationic Bis(Gold) Indenyl Complexes1Mononuclear Palladium(I) Aryl Complexes Perform Cross-Coupling Reactions with Organic Halides14Syntheses and Structures of Cationic Bis(gold) Cyclopentadienyl Complexes1Insights into the mechanism of active catalyst generation for the Pd II (acac) 2 /PPh 3 system in the context of telomerization of 1,3-butadiene3Reactivity studies of butadienesulfinate salts with trinuclear clusters of iron, ruthenium and osmium0Capturing the Hybrid Palladium(I)-Radical Pair Relevant to Photoexcited Palladium Catalysis5Reactivity studies of butadienesulfinate salts with trinuclear clusters of iron, ruthenium and osmium0

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  1. ChemInform Abstract: Dinuclear PdI Complexes with Bridging Allyl and Related Ligands

    ChemInform · 2016-06-01

    Nilay Hazari, Damian P. Hruszkewycz

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  2. Ligand and base additive effects on the reversibility of nucleophilic addition in palladium-catalyzed allylic aminations monitored by nucleophile crossover

    Tetrahedron Letters · 2016-12-22

    Bryan S. Holtzman, Eric T. Roberts, Nicholas S. Caminiti, Jacob A. Fox, Madison B. Goodstein, Staci A. Hill, Zitong B. Jia, Isabelle Nathalie-Marie Leibler, Michael L. Martini, Gina M. Mendolia, Sarah B. Nodder, Molly S. Costanza‐Robinson, Richard C. Bunt

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  3. Synthetic and Mechanistic Interrogation of Pd/Isocyanide-Catalyzed Cross-Coupling: π-Acidic Ligands Enable Self-Aggregating Monoligated Pd(0) Intermediates

    Organometallics · 2017-02-13

    Brandon R. Barnett, Liezel A. Labios, Julia M. Stauber, Curtis E. Moore, Arnold L. Rheingold, Joshua S. Figueroa

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  4. Detection of Palladium(I) in Aerobic Oxidation Catalysis

    Angewandte Chemie International Edition · 2017-02-20

    Jonathan N. Jaworski, Scott D. McCann, Ilia A. Guzei, Shannon S. Stahl

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  5. Detection of Palladium(I) in Aerobic Oxidation Catalysis

    Angewandte Chemie · 2017-02-20

    Jonathan N. Jaworski, Scott D. McCann, Ilia A. Guzei, Shannon S. Stahl

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  6. Mechanism of the Suzuki–Miyaura Cross-Coupling Reaction Mediated by [Pd(NHC)(allyl)Cl] Precatalysts

    Organometallics · 2017-05-24

    Giulia Magi Meconi, Sai V. C. Vummaleti, Jesús Antonio Luque‐Urrutia, Paola Belanzoni, Steven P. Nolan, Heiko Jacobsen, Luigi Cavallo, Miquel Solà, Albert Poater

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  7. Hydrogenation of nitroarenes catalyzed by a dipalladium complex

    Applied Organometallic Chemistry · 2017-07-27

    Ming‐Uei Hung, Shu‐Ting Yang, Mani Ramanathan, Shiuh‐Tzung Liu

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  8. Insights into the Catalytic Activity of [Pd(NHC)(cin)Cl] (NHC=IPr, IPrCl, IPrBr) Complexes in the Suzuki–Miyaura Reaction

    ChemCatChem · 2017-09-06

    Frédéric Izquierdo, Caroline Zinser, Yury V. Minenkov, David B. Cordes, Alexandra M. Z. Slawin, Luigi Cavallo, Fady Nahra, Catherine S. J. Cazin, Steven P. Nolan

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  9. Mechanistic Basis for Efficient, Site-Selective, Aerobic Catalytic Turnover in Pd-Catalyzed C–H Imidoylation of Heterocycle-Containing Molecules

    Journal of the American Chemical Society · 2017-09-24

    Stephen J. Tereniak, Shannon S. Stahl

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  10. Carbon Dioxide Insertion into Group 9 and 10 Metal–Element σ Bonds

    Inorganic Chemistry · 2017-11-08

    Nilay Hazari, Jessica E. Heimann

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  11. Buchwald–Hartwig amination using Pd( i ) dimer precatalysts supported by biaryl phosphine ligands

    Dalton Transactions · 2018-01-01

    Kent O. Kirlikovali, Eunho Cho, Tyler J. Downard, Lilit Grigoryan, Zheng Han, Sooji Hong, Dahee Jung, Jason C. Quintana, Vanessa Reynoso, Sooihk Ro, Yi Shen, Kevin Swartz, Elizabeth Ter Sahakyan, Alex Ian Wixtrom, Brandon Yoshida, Arnold L. Rheingold, Alexander M. Spokoyny

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  12. Dinuclear Nickel(I) and Palladium(I) Complexes for Highly Active Transformations of Organic Compounds

    Molecules · 2018-01-11

    Takahiro Inatomi, Yuji Koga, Kouki Matsubara

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  13. Designing Pd and Ni Catalysts for Cross-Coupling Reactions by Minimizing Off-Cycle Species

    ACS Catalysis · 2018-03-16

    David Balcells, Ainara Nova

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  14. Mechanistic Study of Suzuki–Miyaura Cross‐Coupling Reactions of Amides Mediated by [Pd(NHC)(allyl)Cl] Precatalysts

    ChemCatChem · 2018-04-03

    Guangchen Li, Peng Lei, Michal Szostak, Èric Casals‐Cruañas, Albert Poater, Luigi Cavallo, Steven P. Nolan

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  15. Palladium-Catalyzed Aerobic Homocoupling of Alkynes: Full Mechanistic Characterization of a More Complex Oxidase-Type Behavior

    ACS Catalysis · 2018-07-05

    Alberto Toledo, Ignacio Funes‐Ardoiz, Feliu Maseras, Ana Carmen Albéniz

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  16. C(sp3)–C(sp3) Coupling with a Pd(II) Complex Bearing a Structurally Responsive Ligand

    Organometallics · 2019-04-03

    Kyle M. K. Jackman, Benjamin J. Bridge, Ethan R. Sauvé, Christopher N. Rowley, Cameron H. M. Zheng, James M. Stubbs, Paul D. Boyle, Johanna M. Blacquiere

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  17. Operando Spectroscopic and Kinetic Characterization of Aerobic Allylic C–H Acetoxylation Catalyzed by Pd(OAc)2/4,5-Diazafluoren-9-one

    Journal of the American Chemical Society · 2019-06-11

    Jonathan N. Jaworski, Caitlin V. Kozack, Stephen J. Tereniak, Spring Melody M. Knapp, Clark R. Landis, Jeffrey T. Miller, Shannon S. Stahl

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  18. Development of Palladium Precatalysts that Efficiently Generate LPd(0) Active Species

    Israel Journal of Chemistry · 2019-09-04

    Kevin H. Shaughnessy

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  19. Ligand‐Controlled C−O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights

    Advanced Synthesis & Catalysis · 2019-11-05

    Li Li, Feifei Song, Xiu‐Mei Zhong, Yun‐Dong Wu, Xinhao Zhang, Jiean Chen, Yong Huang

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  20. Bonding and electronic structures in dinuclear (X)[(Ind)M2L2] complexes (M = Ni, Pd, L = CO, PEt3, X = Cl, Allyl, Ind = indenyl, Cp = cyclopentadienyl): analogy between four-electron donor ligands

    Theoretical Chemistry Accounts · 2019-12-16

    Sabri Mecheri, Bachir Zouchoune, Saber‐Mustapha Zendaoui

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  21. Recent advances of dinuclear nickel- and palladium-complexes in homogeneous catalysis

    Chemical Communications · 2020-01-01

    Wentao Xu, Muzi Li, Liancheng Qiao, Jin Xie

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  22. Catalysis with Palladium(I) Dimers

    Angewandte Chemie International Edition · 2020-10-15

    Christoph Fricke, Theresa Sperger, Marvin Mendel, Franziska Schoenebeck

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  23. Catalysis with Palladium(I) Dimers

    Angewandte Chemie · 2020-10-15

    Christoph Fricke, Theresa Sperger, Marvin Mendel, Franziska Schoenebeck

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  24. C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd( i )–Pd( ii ) catalysis vs. Pd( ii ) catalysis

    Chemical Science · 2021-01-01

    Yaohang Cheng, Shijie Yu, Yuhang He, Guanghui An, Guangming Li, Zhen‐Yu Yang

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  25. The Multifaceted Palladium Chemistry of 2,2′-Diphosphinotolanes

    Organometallics · 2021-03-11

    Hannah K. Wagner, Nils Ansmann, Timon Gentner, Hubert Wadepohl, Joachim Ballmann

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  26. Isolation and Catalytic Reactivity of Mononuclear Palladium(I) Complexes

    ChemRxiv · 2021-05-05

    Giang N. Tran, Bailey S. Bouley, Liviu M. Mirica

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  27. Glucopyranoside-Functionalized NHCs-Pd(II)-PEPPSI Complexes: Anomeric Isomerism Controlled and Catalytic Activity in Aqueous Suzuki Reaction

    Catalysis Letters · 2021-05-25

    Zhonggao Zhou, Qian Xie, Jing Li, Yangyang Yuan, Yong Liu, Yulong Liu, Dongliang Lu, Yong‐Rong Xie

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  28. In Situ Formation of Cationic π-Allylpalladium Precatalysts in Alcoholic Solvents: Application to C–N Bond Formation

    ACS Catalysis · 2021-12-20

    Philippe Steinsoultz, Aurélien Bailly, Patrick Wagner, Estefanía Oliva, Martine Schmitt, Laurence Grimaud, Frederic J.‐J. Bihel

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  29. Cationic palladium( ii )-indenyl complexes bearing phosphines as ancillary ligands: synthesis, and study of indenyl amination and anticancer activity

    Dalton Transactions · 2022-01-01

    Enrica Bortolamiol, Francesco Fama, Ziyun Zhang, Nicola Demitri, Luigi Cavallo, Isabella Caligiuri, Flavio Rizzolio, Thomas Scattolin, Fabiano Visentin

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  30. Changes in ligand coordination mode induce bimetallic C–C coupling pathways

    Dalton Transactions · 2022-01-01

    Kyle M. K. Jackman, Guangchao Liang, Paul D. Boyle, Paul M. Zimmerman, Johanna M. Blacquiere

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  31. Monovalent Group 10 Organometallic Complexes

    Elsevier eBooks · 2022-01-01

    Kouki Matsubara

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  32. Palladium-catalyzed Lewis acid-regulated cascade annulation of alkynes with unactivated alkenes to access diverse α-methylene-γ-lactones

    Organic Chemistry Frontiers · 2022-01-01

    Jianxiao Li, Dan He, Bowen Wang, Wenfang Xiong, Chaorong Qi, Huanfeng Jiang

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  33. C−I Selective Sonogashira and Heck Coupling Reactions Catalyzed by Aromatic Triangular Tri‐palladium

    European Journal of Organic Chemistry · 2022-02-22

    Xiaoshuang Wang, Lei Sun, Miaomiao Wang, Giovanni Maestri, Max Malacrìa, Xiang Liu, Yanlan Wang, Lingang Wu

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  34. Carbon–Carbon Bond Coupling of Vinyl Molecules with an Allenyl Ligand at a Diruthenium Complex

    Organometallics · 2022-04-06

    Giulio Bresciani, Stefano Zacchini, Guido Pampaloni, Fabio Marchetti

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  35. METAL-ORGANIC FRAMEWORKS IN RUSSIA: FROM THE SYNTHESIS AND STRUCTURE TO FUNCTIONAL PROPERTIES AND MATERIALS

    Journal of Structural Chemistry · 2022-05-01

    Mikhail Agafonov, Eugeny V. Alexandrov, N.A. Artyukhova, Giyjaz E. Bekmukhamedov, Vladislav A. Blatov, Vera V. Butova, Yakov Maksumovich Gayfulin, A. A. Garibyan, Zufar N. Gafurov, Yulia G. Gorbunova, Larisa G. Gordeeva, Груздев Матвей Сергеевич, А. Н. Гусев, Gleb L. Denisov, Danil N. Dybtsev, Yulia Yu. Enakieva, Alexey A. Kagilev, Artyom O. Kantyukov, Mikhail A. Kiskin, Konstantin A. Kovalenko, Arkadiy M. Kolker, Daniil I. Kolokolov, Yu. M. Litvinova, Anna A. Lysova, Nataliya V. Maksimchuk, Yuri V. Mironov, Yulia Vladimirovna Nelyubina, Valentin V. Novikov, В.И. Овчаренко, Alexandr V. Piskunov, Daniil M. Polyukhov, Vladimir A. Polyakov, Valentina Georgievna Ponomareva, Artem S. Poryvaev, Г.В. Романенко, Alexander V. Soldatov, Marina V. Solovyeva, Alexander G. Stepanov, I. V. Terekhova, O. Yu. Trofimova, Федин Владимир Петрович, Matvey V. Fedin, Oxana A. Kholdeeva, Aslan Yu. Tsivadze, Червонова Ульяна Вадимовна, А. И. Черевко, В. Ф. Шульгин, Е. С. Шутова, Dmitry G. Yakhvarov

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  36. Palladium-Catalyzed Three-Component Selective Aminoallylation of Diazo Compounds

    Organic Letters · 2022-06-03

    Pengcheng Ou, Lei Zhu, Yinghua Yu, Liyao Ma, Xueliang Huang

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  37. Emerging Trends in Cross-Coupling: Twelve-Electron-Based L 1 Pd(0) Catalysts, Their Mechanism of Action, and Selected Applications

    Chemical Reviews · 2022-10-03

    Sharbil J. Firsan, Vilvanathan Sivakumar, Thomas J. Colacot

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  38. Isolation and Characterization of Heteroleptic Mononuclear Palladium(I) Complexes

    Journal of the American Chemical Society · 2022-10-18

    Giang N. Tran, Bailey S. Bouley, Liviu M. Mirica

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  39. Open cell foam materials as Pd reservoirs for Suzuki–Miyaura coupling catalysis at ppb level

    Reaction Chemistry & Engineering · 2023-01-01

    A. Jabbari-Hichri, Amine Bourouina, Pierre‐François Biard, Audrey Denicourt‐Nowicki, Alain Roucoux, Marie‐Line Zanota, Fabrice Campoli, Claude de Bellefon, Valérie Meille

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  40. 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

    Journal of the American Chemical Society · 2023-06-15

    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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  41. Heteroaryl–Heteroaryl Suzuki–Miyaura Cross-Coupling Enabled by Large-but-Flexible Dibenzobarrelene-Derived Pd-NHC Precatalysts

    Organometallics · 2023-07-25

    Mia Guo, Yu Zhang, Meng-Jiao Zhang, Tian Li, Jia-Yi Wu, Feng‐Shou Liu

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  42. Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics

    Chinese Chemical Letters · 2023-10-29

    Yue Sun, Liming Yang, Yaohang Cheng, Guanghui An, Guangming Li

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  43. Cationic Bis(Gold) Indenyl Complexes

    ChemPlusChem · 2024-01-23

    Brady L. Slinger, Jiaqi Zhu, Ross A. Widenhoefer

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  44. Mononuclear Palladium(I) Aryl Complexes Perform Cross-Coupling Reactions with Organic Halides

    CCS Chemistry · 2024-08-05

    Tianqi Xia, Linhong Long, Xuebing B. Leng, Hui Chen, Liang Deng

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  45. Syntheses and Structures of Cationic Bis(gold) Cyclopentadienyl Complexes

    Organometallics · 2024-12-19

    Brady L. Slinger, Jack C. Malek, Ross A. Widenhoefer

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  46. Insights into the mechanism of active catalyst generation for the Pd II (acac) 2 /PPh 3 system in the context of telomerization of 1,3-butadiene

    Chemical Science · 2025-01-01

    Bailey S. Bouley, Dae Young Bae, Sagnik Chakrabarti, Mari S. Rosen, R.D. Kennedy, Liviu M. Mirica

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  47. Reactivity studies of butadienesulfinate salts with trinuclear clusters of iron, ruthenium and osmium

    SSRN Electronic Journal · 2025-01-01

    Maria Rosales-Hoz, Angeles Paz-Sandoval, Aldo S. Estrada‐Montaño, Ottmar R. Reyes-López, Marco A. Leyva

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  48. Capturing the Hybrid Palladium(I)-Radical Pair Relevant to Photoexcited Palladium Catalysis

    Journal of the American Chemical Society · 2025-10-29

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  49. Reactivity studies of butadienesulfinate salts with trinuclear clusters of iron, ruthenium and osmium

    Journal of Organometallic Chemistry · 2026-02-05

    Aldo S. Estrada‐Montaño, Ottmar R. Reyes-López, Marco A. Leyva, M. Angeles Paz‐Sandoval, Maria Rosales-Hoz

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