A5046611375- Sulfur-Based Synthesis Techniques
- Fluorine in Organic Chemistry
- Radical Photochemical Reactions
- Catalytic C–H Functionalization Methods
- Inorganic Fluorides and Related Compounds
- X-ray Diffraction in Crystallography
- N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
- Cyclopropane Reaction Mechanisms
- Crystallization and Solubility Studies
- Synthesis and Catalytic Reactions
- Medical Imaging Techniques and Applications
- Chemical Reactions and Isotopes
University of Oxford
2019-2022
Princeton University
2022
Oxford Research Group
2019-2021
Abstract A facile method for the regioselective hydrodifluoromethylation of alkenes is reported using difluoroacetic acid and phenyliodine(III) diacetate in tetrahydrofuran under visible‐light activation. This metal‐free approach stands out as it uses inexpensive reagents, does not require a photocatalyst, displays broad functional group tolerance. The procedure also operationally simple scalable, provides access one step to high‐value building blocks application medicinal chemistry.
Abstract Sulfonyl chlorides are inexpensive reactants extensively explored for functionalization, but never considered radical hydrosulfonylation of alkenes. Herein, we report that tris(trimethylsilyl)silane is an ideal hydrogen atom donor enabling highly effective photoredox‐catalyzed electron‐deficient alkenes with sulfonyl chlorides. To increase the generality this transformation, polarity‐reversal catalysis (PRC) was successfully implemented bearing alkyl substituents. This late‐stage...
Single electron reduction is more challenging for sulfamoyl chlorides than sulfonyl chlorides. However, and can be easily activated by Cl-atom abstraction a silyl radical with similar rates. This latter mode of activation was therefore selected to access aliphatic sulfonamides, applying single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, photocatalyst Eosin Y. late-stage functionalization protocol generates molecules as complex sulfonamide-containing...
A process for the direct hydrofluoromethylation of alkenes is reported first time. This straighforward silyl radical-mediated reaction utilises CH2FI as a non-ozone depleting reagent, traditionally used in electrophilic, nucleophilic and carbene-type chemistry, but not CH2F radical source. By circumventing challenges associated with high reduction potential being closer to CH3I than CF3I, harnessing instead favourable bond dissociation energy C-I bond, we demonstrate that feedstock...
We introduce here a two-component annulation strategy that provides access to diverse collection of five- and six-membered saturated heterocycles from aryl alkenes family redox-active radical precursors bearing tethered nucleophiles. This transformation is mediated by combination an Ir(III) photocatalyst Brønsted acid under visible-light irradiation. A reductive proton-coupled electron transfer generates reactive which undergoes addition alkene. Then, oxidative radical-polar crossover step...
Abstract Sulfonyl chlorides are inexpensive reactants extensively explored for functionalization, but never considered radical hydrosulfonylation of alkenes. Herein, we report that tris(trimethylsilyl)silane is an ideal hydrogen atom donor enabling highly effective photoredox‐catalyzed electron‐deficient alkenes with sulfonyl chlorides. To increase the generality this transformation, polarity‐reversal catalysis (PRC) was successfully implemented bearing alkyl substituents. This late‐stage...
Abstract A facile method for the regioselective hydrodifluoromethylation of alkenes is reported using difluoroacetic acid and phenyliodine(III) diacetate in tetrahydrofuran under visible‐light activation. This metal‐free approach stands out as it uses inexpensive reagents, does not require a photocatalyst, displays broad functional group tolerance. The procedure also operationally simple scalable, provides access one step to high‐value building blocks application medicinal chemistry.
Sulfonamides are prevalent motifs in marketed drugs and natural products. Their synthesis represents a great interest to the pharmaceutical industry, due their unique biological properties. Recently, several methods for of aryl sulfonamides have been developed, but little effort has focused on developing one-step methodologies access flanked by two alkyl groups. This protocol describes practical facile method net hydrosulfamoylation electron-deficient alkenes using sulfamoyl chlorides as...
Sulfonamides are prevalent motifs in marketed drugs and natural products. Their synthesis represents a great interest to the pharmaceutical industry, due their unique biological properties. Recently, several methods for of aryl sulfonamides have been developed, but little effort has focused on developing one-step methodologies access flanked by two alkyl groups. This protocol describes practical facile method net hydrosulfamoylation electron-deficient alkenes using sulfamoyl chlorides as...