Benson Jelier

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Jelier

First Name

Benson

ORCID

0000-0002-5531-0431

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Publications 1 - 9 of 9

Pyridyl Radical Cation for C−H Amination of Arenes
Rössler, Simon; Jelier, Benson; Tripet, Pascal F.; et al. (2019)
Angewandte Chemie. International Edition
Trifluoromethyl Derivatives of Benzooxatellurole
Pietrasiak, Ewa; Baxter, Amanda F.; Jelier, Benson; et al. (2019)
Helvetica Chimica Acta
Halogenation and perfluoroalkylation chemistry using hypervalent halogen compounds
Katayev, Dmitry; Jelier, Benson; Togni, Antonio (2018)
PATAI'S Chemistry of Functional Groups
Synthetic Diversity from a Versatile and Radical Nitrating Reagent
Zhang, Kun; Jelier, Benson; Passera, Alessandro; et al. (2019)
Chemistry - A European Journal
Exposing the Origins of Irreproducibility in Fluorine NMR Spectroscopy
Rosenau, Carl Philipp; Jelier, Benson; Gossert, Alvar D.; et al. (2018)
Angewandte Chemie. International Edition
Profiling the oxidative activation of DMSO-F6 by pulse radiolysis and translational potential for radical C–H trifluoromethylation
Santschi, Nico; Jelier, Benson; Stähelin, Samuel; et al. (2019)
Organic & biomolecular chemistry
The oxidative activation of the perfluorinated analogue of dimethyl sulfoxide, DMSO-F6, by hydroxyl radicals efficiently produces trifluoromethyl radicals based on pulse radiolysis, laboratory scale experiments, and comparison of rates of reaction for analogous radical systems. In comparison to commercially available precursors, DMSO-F6 proved to be more stable, easier to handle and overall more convenient than leading F3C-reagents and may therefore be an ideal surrogate to study F3C radicals for time-resolved kinetics studies. In addition, we present an improved protocol for the preparation of this largely unexplored reagent.
Radical α-Trifluoromethoxylation of Ketones under Batch and Flow Conditions by Means of Organic Photoredox Catalysis
Duhail, Thibaut; Bortolato, Tommaso; Mateos, Javier; et al. (2021)
Organic Letters
The first light-driven method for the α-trifluoromethoxylation of ketones is reported. Enol carbonates react with N-trifluoromethoxy-4-cyano-pyridinium, using the photoredox catalyst 4-CzIPN under 456 nm irradiation, affording the α-trifluoromethoxy ketones in ≤50% isolated yield and complete chemoselectivity. As shown by 29 examples, the reaction is general and proceeds very rapidly under batch (1 h) and flow conditions (2 min). Diverse product manipulations demonstrate the synthetic potential of the disclosed method in accessing elusive trifluoromethoxylated bioactive ingredients.
Determining the predominant tautomeric structure of iodine-based group-transfer reagents by 17O NMR spectroscopy
Santschi, Nico; Pitts, Cody R.; Jelier, Benson; et al. (2018)
Beilstein Journal of Organic Chemistry
Cyclic benziodoxole systems have become a premier scaffold for the design of electrophilic transfer reagents. A particularly intriguing aspect is the fundamental II–IIII tautomerism about the hypervalent bond, which has led in certain cases to a surprising re-evaluation of the classic hypervalent structure. Thus, through a combination of 17O NMR spectroscopy at natural abundance with DFT calculations, we establish a convenient method to provide solution-phase structural insights for this class of ubiquitous reagents. In particular, we confirm that Shen’s revised, electrophilic SCF3-transfer reagent also adopts an "acyclic" thioperoxide tautomeric form in solution. After calibration, the approach described herein likely provides a more general and direct method to distinguish between cyclic and acyclic structural features based on a single experimental 17O NMR spectrum and a computationally-derived isotropic shift value. Furthermore, we apply this structural elucidation technique to predict the constitution of an electrophilic iodine-based cyano-transfer reagent as an NC–I–O motif and study the acid-mediated activation of Togni's trifluoromethylation reagent.
Development and Molecular Understanding of a Pd-Catalyzed Cyanation of Aryl Boronic Acids Enabled by High-Throughput Experimentation and Data Analysis
De Jesus Silva, Jordan; Bartalucci, Niccolò; Jelier, Benson; et al. (2021)
Helvetica Chimica Acta
A synthetic method for the palladium-catalyzed cyanation of aryl boronic acids using bench stable and non-toxic N-cyanosuccinimide has been developed. High-throughput experimentation facilitated the screen of 90 different ligands and the resultant statistical data analysis identified that ligand sigma-donation, pi-acidity and sterics are key drivers that govern yield. Categorization into three ligand groups - monophosphines, bisphosphines and miscellaneous - was performed before the analysis. For the monophosphines, the yield of the reaction increases for strong sigma-donating, weak pi-accepting ligands, with flexible pendant substituents. For the bisphosphines, the yield predominantly correlates with ligand lability. The applicability of the designed reaction to a wider substrate scope was investigated, showing good functional group tolerance in particular with boronic acids bearing electron-withdrawing substituents. This work outlines the development of a novel reaction, coupled with a fast and efficient workflow to gain understanding of the optimal ligand properties for the design of improved palladium cross-coupling catalysts.

Publications 1 - 9 of 9

Benson Jelier

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