Eric C. Keske

ORCID: 0000-0002-7129-1189
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About
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Research Areas
  • X-ray Diffraction in Crystallography
  • Crystallization and Solubility Studies
  • Catalytic Cross-Coupling Reactions
  • N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
  • Synthetic Organic Chemistry Methods
  • Asymmetric Hydrogenation and Catalysis
  • Organoboron and organosilicon chemistry
  • Crystallography and molecular interactions
  • Organometallic Complex Synthesis and Catalysis
  • Molecular Junctions and Nanostructures
  • Catalytic C–H Functionalization Methods
  • Metal complexes synthesis and properties
  • Tryptophan and brain disorders
  • Cyclopropane Reaction Mechanisms
  • Oxidative Organic Chemistry Reactions
  • Metal-Catalyzed Oxygenation Mechanisms
  • Click Chemistry and Applications
  • Carbon dioxide utilization in catalysis
  • MXene and MAX Phase Materials
  • Chemical Synthesis and Analysis
  • Radical Photochemical Reactions
  • Catalysis for Biomass Conversion
  • Pharmacological Receptor Mechanisms and Effects
  • Treatment of Major Depression
  • Sulfur-Based Synthesis Techniques

Trent University
2021-2024

University of Toronto
2019-2023

University Health Network
2021

Krembil Research Institute
2021

University of Edinburgh
2018

Queen's University
2011-2016

Abstract 1,2,3‐Triazolylidene‐based mesoionic carbene boranes have been synthesized in a convenient one‐pot protocol from the corresponding 1,2,3‐triazolium salts, base, and borane. Borenium ions are obtained by hydride abstraction serve as catalysts mild hydrogenation reactions of imines unsaturated N‐heterocycles at ambient pressure temperature.

10.1002/anie.201409250 article EN Angewandte Chemie International Edition 2015-01-13

The development of fluorinated sulfone derivatives as versatile electrophiles for Suzuki–Miyaura cross-coupling reactions is described. Introducing electron-withdrawing groups on the aryl ring facilitates Pd-catalyzed activation C–SO2 bonds. Cross-coupling with are reported, leading to a variety multiply arylated products in good yields. reactivity this unusual electrophile benchmarked versus common and its use iterative cross-couplings concise synthesis biologically active molecules

10.1021/acscatal.6b03434 article EN ACS Catalysis 2016-12-19

New mono- and bimetallic 1,2,3-triazol-5-ylidene mesoionic carbene (MIC) complexes of Pd have been synthesized, isolated, characterized. We described the synthesis a bis(MIC) complex via transmetalation from Ag-MIC two PEPPSI-type which are directly available their respective triazolium salts by treatment with PdCl2 in pyridine. The X-ray structures reported for all herein. Interestingly, each exhibits various secondary noncovalent interactions solid state general type C–H···Cl, appear to be...

10.1021/om3005228 article EN Organometallics 2012-08-30

New mono- and bidentate 1,2,3-triazol-5-ylidene mesoionic carbene (MIC) ligands have been synthesized reacted with silver oxide, forming cationic 1:2 2:2 Ag:MIC ([AgL2]Br [Ag2L2][Ag2Br4]) complexes, respectively. These complexes isolated characterized. They were further found to be potent transmetalation agents toward rhodium, resulting in the preparation of bimetallic rhodium complexes. The reaction Ag:L complex [Rh(COD)2]BF4 results first reported example a MIC complex. This was fully...

10.1021/om201104f article EN Organometallics 2011-12-16

Drei Gase, ein Kristall: Rhodium-NHC-Komplexe können aufeinander folgende Einkristall-zu-Einkristall-Umwandlungen unter selektivem und nichtreversiblem Ligandenaustausch eingehen (siehe Bild). Bei langsamer Diffusion von O2 wandelt sich Distickstoffkomplex in einen Disauerstoffkomplex um, aus dem dann durch CO verdrängt werden kann. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents peer-reviewed, but not copy-edited or typeset. They...

10.1002/ange.201103316 article EN Angewandte Chemie 2011-07-08

Dimeric rhodium N-heterocyclic carbene complexes are demonstrated to be effective catalyst precursors for directed C–H borylation reactions at room temperature.

10.1039/c4cc02499k article EN Chemical Communications 2014-01-01

Abstract 1,2,3‐Triazolylidene‐based mesoionic carbene boranes have been synthesized in a convenient one‐pot protocol from the corresponding 1,2,3‐triazolium salts, base, and borane. Borenium ions are obtained by hydride abstraction serve as catalysts mild hydrogenation reactions of imines unsaturated N‐heterocycles at ambient pressure temperature.

10.1002/ange.201409250 article EN Angewandte Chemie 2015-01-13

The mechanism the Chatani–Tobisu rhodium-catalyzed decyanative silylation of aryl nitriles by hexamethyldisilane (Me3Si-SiMe3) has been investigated in situ NMR spectroscopy. production Ar-SiMe3 evolves three distinct phases: slow catalyst induction is followed a period rapidly accelerating turnover and then, after approximately turnovers, onset progressive inhibition. processes giving rise to these phenomena have elucidated isotopic labeling (13C/15N) kinetic analysis, it shown that,...

10.1021/acscatal.8b02809 article EN ACS Catalysis 2018-08-14

Dimeric rhodium complexes with various N-heterocyclic carbene (NHC) ligands have been synthesized and fully characterized. X-ray analysis unambiguously confirms the bimetallic nature of these complexes, in all cases one molecule ethylene is coordinated to each metal center an η2-fashion. The Rh atoms are also NHC ligand interconnected by two μ-chlorine bridges. dimeric most likely stabilized due significant steric bulk around centers provided ligands. Consistent this, modulating properties...

10.1021/om200710y article EN Organometallics 2011-11-15

The synthesis, structure determination and oxidative stability of novel Rh-NHC complexes which feature pyridine-derived ligands have been described. All described herein were synthesized from common dinuclear precursors general [Rh(NHC)(L)Cl](2), where L is a monodentate olefin. We demonstrate that the use these critical for formation all since related cyclooctadiene containing ([Rh(NHC)(COD)Cl]) completely unreactive under identical conditions. further with formula [Rh(NHC)(olefin)(Py)Cl]...

10.1039/c2dt32095a article EN Dalton Transactions 2012-10-23

Mononuclear cationic rhodium complexes of dioxygen have been synthesized and characterized. Crystallographic, spectroscopic, computational results support the conclusion that these are best described as RhIII{O22–} (rhodium(III) peroxo) complexes, in contrast to recently reported neutral analogues RhI{1O2} adducts. The nature ligand trans O2 is crucial defining electronic RhO2 bonding. It determined π-donor ligands such halides—in conjunction with sufficient steric bulk—can stabilize...

10.1021/om300766x article EN Organometallics 2012-10-05

Rhodium complexes functionalized by N-heterocyclic carbene ligands react with dioxygen to form adducts. Depending on the specifics of ancillary ligands, oxygen binds Rh either as a peroxide fully oxidized Rh(III) complex, or singlet in Rh(I) square planar complex. We have shown through analysis series compounds, some previously published and novel, that presence additional would support formation an octahedral geometry, typically found complexes, is critical for peroxide. In addition, we...

10.1039/c3dt32264e article EN Dalton Transactions 2013-01-01

Palladium N-heterocyclic carbene (NHC) complexes of the general type [(NHC)Pd(allyl)Cl] are investigated as precatalysts in Hiyama reaction aryl chlorides with phenyl trimethoxysilanes. High yields biaryls products obtained from featuring electron withdrawing groups using coordinated to NHC ligands sterically smaller wingtip (IMes and SIMes). Unactivated appeared be poor substrates this reaction. A mechanistic proposal which we believe explains activity is outlined based on situ analysis by...

10.1021/acs.organomet.3c00312 article EN Organometallics 2023-11-09

Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising therapeutic target in cancer immunotherapy and neurological disease. Thus, searching for highly active inhibitors use human cancers now focus of widespread research development efforts. In this study, we report the structure-based design 2-(5-imidazolyl)indole derivatives, series novel IDO1 which have been designed synthesized based on our previous study using N1-substituted 5-indoleimidazoles. Among these, identified one with strong...

10.1002/cmdc.202100107 article EN ChemMedChem 2021-03-24

N-Heterocyclic carbenes (NHCs) featuring 2,6-dialkoxyphenyl wingtip groups are synthesized, and their coordination chemistry properties studied. Linear [(NHC)CuCl] complexes composed of ligands synthesized herein were characterized by X-ray crystallography used to analyze the ligand steric parameters. We demonstrate that use different alkyl halides in preparation these results NHCs sterically tunable potentially capable hemilability. Furthermore, electronic assessed computational methods,...

10.1021/acs.organomet.4c00369 article EN Organometallics 2024-12-02

This work describes a new method for the preparation of copper N-heterocyclic carbene (NHC) complexes, which is conducted under air with mild conditions, using bench-stable precursors and weak base (NEt 3 ). Under optimized complexes were prepared in short reaction times 1 h, giving moderate to good yields after purification by column chromatography. Commonly utilized NHC–HCl salts found be applicable reacting CuCl or CuI [(NHC)CuX]-type (X = Cl, I). study adds growing literature...

10.1139/cjc-2022-0229 article EN Canadian Journal of Chemistry 2022-11-10

Abstract Three new Ru complexes with N‐P(OH)‐N donor ligands were synthesized and characterized. A ruthenium complex a ligand quinolinyl side arms exhibited monodentate coordination through the phosphorus atom an intramolecular POH⋅⋅⋅N(quinolinyl) hydrogen bond but no interaction between nitrogen donors center. Two pentamethylcyclopentadienyl pyridyl fac‐ κ 3 ‐NPN’ tridentate to metal center, one interionic POH⋅⋅⋅FPF 5 in crystal. paramagnetic nickel [Ni (N‐P(O)‐N) 4 ] cluster was also...

10.1002/zaac.202100073 article EN Zeitschrift für anorganische und allgemeine Chemie 2021-05-07
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