A5081181426- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Radical Photochemical Reactions
- Innovative Microfluidic and Catalytic Techniques Innovation
- Sulfur-Based Synthesis Techniques
- Catalytic C–H Functionalization Methods
- Advanced Photocatalysis Techniques
- Catalytic Cross-Coupling Reactions
- Click Chemistry and Applications
- Chemical Synthesis and Analysis
- Fluorine in Organic Chemistry
- Scheduling and Optimization Algorithms
- Luminescence and Fluorescent Materials
- Enzyme Catalysis and Immobilization
- Biochemical and Molecular Research
- Cyclopropane Reaction Mechanisms
- Ion Channels and Receptors
- Assembly Line Balancing Optimization
- Manufacturing Process and Optimization
- HIV/AIDS drug development and treatment
- Inflammasome and immune disorders
- Carbohydrate Chemistry and Synthesis
- Advanced Nanomaterials in Catalysis
- Microbial Natural Products and Biosynthesis
- Caching and Content Delivery
Janssen (Belgium)
2017-2024
Virginia Commonwealth University
2020-2021
University of Richmond
2021
A continuous-flow, visible-light-promoted method has been developed to overcome the limitations of iron-catalyzed Kumada-Corriu cross-coupling reactions. variety strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes' residence time, considerably enhancing applicability this reaction. The robustness protocol was demonstrated on multigram scale, thus providing...
The merging of photoredox and transition-metal catalysis has become one the most attractive approaches for carbon-carbon bond formation. Such reactions require use two organo-transition-metal species, which acts as a photosensitizer other cross-coupling catalyst. We report herein an exogenous-photosensitizer-free photocatalytic process formation bonds by direct acceleration well-known nickel-catalyzed Negishi that is based on naturally abundant metals. This finding will open new avenues in...
We report a continuous-flow protocol for the trifluoromethylation of arenes, heteroarenes, and benzofused heterocycles. This photoredox methodology relies on use solid sodium trifluoromethanesulfinate (CF3SO2Na) as trifluoromethylating agent iridium complex [Ir{dF(CF3)ppy}2](dtbpy)]PF6 catalyst. A diverse set highly functionalized heterocycles proved compatible with methodology, moderate to good yields were obtained within 30 minutes residence time.
Abstract A visible‐light‐induced Negishi cross‐coupling is enabled by the activation of a Pd 0 –Zn complex. With this photocatalytic method, scope deactivated aryl halides that can be employed in coupling was significantly expanded. NMR experiments conducted presence and absence light confirmed formation palladium–zinc complex key for accelerating oxidative addition step.
Abstract Herein, we report the de novo synthesis and characterization of a series substituted bithiophene derivatives as novel inexpensive organic photocatalysts. DFT calculations were used to predict priori their absorption spectra redox potentials, which then confirmed with empirical data. The photocatalytic activity this class photoredox catalyst was demonstrated in two visible‐light mediated strategies for C−H functionalization heteroarenes. implementation these continuous‐flow...
We report herein the transfer of dual photoredox and nickel catalysis for C(sp2)C(sp3) cross coupling form batch to flow. This new procedure clearly improves scalability previous reaction by reactor's size operating time reduction, allows preparation interesting compounds drug discovery in multigram amounts.
The scale up of light-induced nickel-catalyzed Negishi reactions is reported herein, with output rates reaching multigram quantities per hour. This level throughput suitable to support preclinical medicinal chemistry programs in late lead optimization, where tens grams hundreds final product needed. Adjusting reaction times and concentrations was critical achieving this robust output. example demonstrates how visible photochemistry use solid metal reagent can be used the progress followed by...
An economical synthesis of lamivudine was developed by employing a new method to establish the stereochemistry about heterocyclic oxathiolane ring. Toward this end, an inexpensive and readily accessible lactic acid derivative served dual purpose activating carbohydrate's anomeric center for N-glycosylation transferring stereochemical information substrate simultaneously. Both enantiomers are available, either β-enantiomer in challenging class 2′-deoxynucleoside active pharmaceutical...
Abstract Increasing F sp 3 in drug molecules is of high importance the pharmaceutical industry to escape flatland. However, there a lack diverse methods introduce C(sp ) into molecule library synthesis. In this work, we report combination continuous flow chemistry with photochemistry create an automated platform for synthesis using halogen atom transfer (XAT) reaction increase molecules. The has broad scope alkyl halides and electron deficient alkenes. We 84 compounds productivity 1.5...
In drug discovery, automated library synthesis has traditionally focussed on established chemistry such as amide formation or Suzuki coupling. However, to explore a broader chemical space, recent protocols have emphasized increasing the fraction of sp3 hybridized carbons move beyond limitations planar molecules. Herein we present novel approach for multistep in continuous flow, enabling linkage three different elements combinatorial way. To achieve this synthesis, employed nine reactions...
In drug discovery, traditional automated library synthesis has typically involved single-step synthetic procedures targeting a single vector of interest. However, achieving greater structural diversity requires exploring multistep and multivectorial approaches. These methodologies enable the preparation compounds with varying structures in experiment. Here, we present novel method for continuous flow. This approach offers unique opportunities, such as linkers between two defined vectors or...
Abstract The merging of photoredox and transition‐metal catalysis has become one the most attractive approaches for carbon–carbon bond formation. Such reactions require use two organo‐transition‐metal species, which acts as a photosensitizer other cross‐coupling catalyst. We report herein an exogenous‐photosensitizer‐free photocatalytic process formation bonds by direct acceleration well‐known nickel‐catalyzed Negishi that is based on naturally abundant metals. This finding will open new...
Abstract A continuous‐flow, visible‐light‐promoted method has been developed to overcome the limitations of iron‐catalyzed Kumada–Corriu cross‐coupling reactions. variety strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes’ residence time, considerably enhancing applicability this reaction. The robustness protocol was demonstrated on multigram scale, thus...
Abstract A visible‐light‐induced Negishi cross‐coupling is enabled by the activation of a Pd 0 –Zn complex. With this photocatalytic method, scope deactivated aryl halides that can be employed in coupling was significantly expanded. NMR experiments conducted presence and absence light confirmed formation palladium–zinc complex key for accelerating oxidative addition step.
Recently, we demonstrated that ylidenemalononitriles (YMs) react with amines to form cyclic amidines and the starting linear YMs are nonemissive in solution fluorescent. These turn-on systems were of interest us because their potential as biosensors synthons for accessing functionalized pyridines. While our original method was promising, several limitations persisted, including access more polar-solvent-soluble structures well increased control over rate cyclization. Herein, report a new...
A mild and solvent-free methodology to obtain a scope of multi-substituted pyridines at room temperature is presented. One the resulting amino-nicotinonitriles exhibits preliminary evidence aggregation-induced emission (AIE).
Zwei häufig vorkommende Metalle, …… Zink und Nickel, ermöglichen unter Bestrahlung mit sichtbarem Licht die Bildung neuer C(sp3)-C(sp2)-Bindungen. In ihrer Zuschrift auf S. 8609 erläutern J. Alcázar et al., wie diese Reaktionsbedingungen zu einer direkten Beschleunigung der Nickel-katalysierten Negishi-Kreuzkupplung führen, ohne dass ein zusätzlicher Photosensibilisator nötig wäre.