A5031595016- Radical Photochemical Reactions
- Catalytic C–H Functionalization Methods
- Oxidative Organic Chemistry Reactions
- Asymmetric Hydrogenation and Catalysis
- Fluorine in Organic Chemistry
- Sulfur-Based Synthesis Techniques
- Carbon dioxide utilization in catalysis
- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Asymmetric Synthesis and Catalysis
- Synthesis and Catalytic Reactions
- Inorganic Fluorides and Related Compounds
- Synthetic Organic Chemistry Methods
- Catalytic Cross-Coupling Reactions
- CO2 Reduction Techniques and Catalysts
- Chemical Reactions and Isotopes
- Ammonia Synthesis and Nitrogen Reduction
- Organometallic Complex Synthesis and Catalysis
- Multiple Myeloma Research and Treatments
- Chemical Reaction Mechanisms
- Protein Degradation and Inhibitors
- Chemical Synthesis and Analysis
- Innovative Microfluidic and Catalytic Techniques Innovation
- Axial and Atropisomeric Chirality Synthesis
- Chemical synthesis and alkaloids
Age UK
2019-2024
GlaxoSmithKline (United Kingdom)
2017-2024
University of Strathclyde
2023
North Hertfordshire College
2019-2021
GlaxoSmithKline (Croatia)
2019
University of Oxford
2008-2015
Universidade de Santiago de Compostela
2009-2015
Queen's University Belfast
2008
The rhodium-catalyzed methylation of ketones has been accomplished using methanol as the methylating agent and hydrogen-borrowing method. sequence is notable for relatively low temperatures that are required ability reaction system to form α-branched products with ease. Doubly alkylated can be prepared from methyl two different alcohols by a sequential one-pot iridium- process.
Ferrocene, Fc, and cobaltocenium hexafluorophosphate, CcPF6, have been recommended for use as internal reference redox couples in room-temperature ionic liquids (RTILs), well more conventional aprotic solvents. In this study, the electrochemical behavior of Fc CcPF6 is reported eight commonly used RTILs; [C2mim][NTf2], [C4mim][NTf2], [C4mim][BF4], [C4mim][PF6], [C4mim][OTf], [C4mim][NO3], [C4mpyrr][NTf2], [P14,6,6,6][FAP], where [Cnmim]+ = 1-butyl-3-methylimidazolium, [NTf2]-...
Reported herein is the use of catalytic [{Ir(cod)Cl}2 ] to facilitate hydrogen-borrowing reactions ketone enolates with methanol at 65 °C. An oxygen atmosphere accelerates process, and when combined a bulky monodentate phosphine ligand, interrupts cycle by preventing enone reduction. Subsequent addition pro-nucleophiles reaction mixture allowed one-pot methylenation/conjugate protocol be developed, which greatly expands range products that can made this methodology.
Fluorinated alkyl groups are important motifs in bioactive compounds, positively influencing pharmacokinetics, potency and conformation. The oxidative difluorination of alkenes represents an strategy for their preparation, yet current methods limited alkene-types tolerance electron-rich, readily oxidized functionalities, as well safety scalability. Herein, we report a method the number unactivated that is tolerant electron-rich functionality, giving products otherwise unattainable. Key to...
sulfinamides, sulfonamides, and sulfonimidamides are in-demand motifs in medicinal chemistry, yet methods for the synthesis of alkyl variants that start from simple, readily available feedstocks scarce. In addition, bespoke syntheses each class molecules usually needed. this report, we detail these three distinct sulfur functional groups, using structurally diverse carboxylic acids as starting materials. The method harnesses radical generation acridine photocatalysts 400 nm light with...
We report a general procedure for the direct mono- and di-hydrodefluorination of ArCF
A practical electrochemical method for the rapid, safer, and mild synthesis of tertiary hindered alkyl fluorides from carboxylic acids has been developed without need hydrofluoric acid salts or non-glass reactors. In this anodic fluorination, collidinium tetrafluoroborate acts as both supporting electrolyte fluoride donor. wide range functional groups shown to be compatible, possibility scale-up using flow electrochemistry also demonstrated.
Herein, we report the decarboxylative Minisci heteroarylation of bicyclo[1.1.1]pentane (BCP) and 2-oxabicyclo[2.1.1]hexane (oBCH) derivatives at bridge positions. In an operationally simple, photocatalyst-free process, free carboxylic acids are directly coupled with nonprefunctionalized heteroarenes to provide rare examples polysubstituted BCP oBCH in synthetically useful yields. Additionally, impact core on physicochemical properties a representative example compared those its all-aromatic...
The bromodomain and extraterminal (BET) family of bromodomain-containing proteins are important regulators the epigenome through their ability to recognize N-acetyl lysine (KAc) post-translational modifications on histone tails. These interactions have been implicated in various disease states and, consequently, disruption BET-KAc binding has emerged as an attractive therapeutic strategy with a number small molecule inhibitors now under investigation clinic. However, until utility these...
Electrochemical transformations involve complex parameter interactions, ranging from universal chemistry variables such as solvent and reagents to specialist factors including electrode material current density. Hence, the development of a robust scale-independent electrochemical reaction can currently be challenge. High-throughput experimentation (HTE) is an enabling method for optimization robustness testing. Here we provide industrial academic perspective on state art combination HTE with...
Synthetically versatile alkyl sulfinates can be prepared from readily available amines, using Katritzky pyridinium salt intermediates. In a catalyst-free procedure, primary, secondary, and benzylic radicals are generated by photoinduced or thermally induced single-electron transfer (SET) an electron donor-acceptor (EDA) complex, trapped SO2 to generate sulfonyl radicals. Hydrogen atom (HAT) Hantzsch ester gives sulfinate products, which used prepare selection of medicinal chemistry relevant...
Hydrogenation reactions are staple transformations commonly used across scientific fields to synthesise pharmaceuticals, natural products, and various functional materials. However, the vast majority of these require use a toxic costly catalyst leading unpractical, hazardous often functionally limited conditions. Herein, we report new, general, practical, efficient, mild high-yielding hydrogen-free electrochemical method for reduction alkene, alkyne, nitro azido groups. Finally, this has...
Oxygen-atom transfer reactions are a prominent class of synthetic redox that often use high-energy oxygen-atom donor reagents. Electrochemical methods can bypass these reagents by using water as the source oxygen atoms through pathways involving direct or indirect (mediated) electrolysis. Here, manganese porphyrins and related mediators shown to be effective molecular electrocatalysts for selective oxidation thioethers sulfoxides, without overoxidation sulfone. The proceed proton-coupled Mn
Bicyclo[2.1.1]hexanes have emerged as valuable scaffolds for the design of new pharmaceutical and agrochemical active ingredients. These structures can be efficiently synthesized via [2π + 2σ] photocycloadditions; however, control over absolute stereochemistry these strain-releasing reactions has remained challenging. Herein, we demonstrate that Brønsted acid catalyzed chromophore activation C-acyl imidazoles enables highly enantioselective photocycloadditions. Because this approach is...
Abstract The rhodium‐catalyzed methylation of ketones has been accomplished using methanol as the methylating agent and hydrogen‐borrowing method. sequence is notable for relatively low temperatures that are required ability reaction system to form α‐branched products with ease. Doubly alkylated can be prepared from methyl two different alcohols by a sequential one‐pot iridium‐ process.
Isothiocyanates are ubiquitous building blocks used across the fields. Nevertheless, their classical syntheses very often rely on use of toxic and expensive reagents. Herein, we report a new practical, mild, high-yielding, supporting-electrolyte-free electrochemical method for preparation aliphatic aromatic isothiocyanates from amine carbon disulfide.
Abstract Recent studies by Stoltz, Grubbs et al. have shown that triethylsilane and potassium tert ‐butoxide react to form a highly attractive versatile system shows (reversible) silylation of arenes heteroarenes as well reductive cleavage C−O bonds in aryl ethers C−S thioethers. Their extensive mechanistic indicate complex network reactions with number possible intermediates mechanisms, but their likely feature silyl radicals undergoing addition S H 2 reactions. This paper focuses on the...
Machine learning approaches promise to accelerate and improve success rates in medicinal chemistry programs by more effectively leveraging available data guide a molecular design. A key step of an automated computational design algorithm is molecule generation, where the machine required high-quality, drug-like molecules within appropriate chemical space. Many algorithms have been proposed for generation; however, challenge how assess validity resulting molecules. Here, we report three...
An electrochemical method for the green and practical synthesis of a broad range substituted isoxazoline cores is presented. Both aryl more challenging alkyl aldoximes are converted to desired in an electrochemically enabled regio- diastereoselective reaction with electron-deficient alkenes. Additionally, in-situ monitoring methods compatible electrochemistry equipment have been developed order probe pathway. Supporting analyses from kinetic (time-course) modelling density functional theory...
Abstract Reported herein is the use of catalytic [{Ir(cod)Cl} 2 ] to facilitate hydrogen‐borrowing reactions ketone enolates with methanol at 65 °C. An oxygen atmosphere accelerates process, and when combined a bulky monodentate phosphine ligand, interrupts cycle by preventing enone reduction. Subsequent addition pro‐nucleophiles reaction mixture allowed one‐pot methylenation/conjugate protocol be developed, which greatly expands range products that can made this methodology.
The 3-substituted chromane core is found in several bioactive natural products. Herein, we describe a route to 3-fluorinated chromanes from allylic phenol ethers. Our external oxidant-free approach takes advantage of an electrochemical generation hypervalent iodine species, difluoro-λ3-tolyl iodane, which mediates the alkene fluoroarylation. High yields and selectivity for this transformation are achieved electron poor substrates. redox chemistry has been characterized iodane presence...
The selective hetero-dihalogenation of alkenes provides useful building blocks for a broad range chemical applications. Unlike homo-dihalogenation, reactions, especially fluorohalogenation, are underdeveloped. Current approaches combine an electrophilic halogen source with nucleophilic source, which necessarily leads to anti-addition, and regioselectivity has only been achieved using highly activated alkenes. Here we describe alternative, nucleophile-nucleophile approach that adds chloride...