A5062505975- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Fluorine in Organic Chemistry
- Oxidative Organic Chemistry Reactions
- Asymmetric Synthesis and Catalysis
- Cyclopropane Reaction Mechanisms
- Catalytic C–H Functionalization Methods
- Chemical Synthesis and Analysis
- Inorganic Fluorides and Related Compounds
- Radical Photochemical Reactions
- Carbohydrate Chemistry and Synthesis
- Synthesis and Catalytic Reactions
University of Münster
2021-2024
Analytisches Laboratorium
2021
ETH Zurich
2019
An I(I)/(III) catalysis strategy to construct an enantioenriched fluorinated isostere of the
The success of saturated, fluorinated heterocycles in contemporary drug discovery provides a stimulus for creative endeavor main group catalysis. Motivated by the ubiquity isochromans across bioactive small molecule spectrum, prominence anomeric effect regulating conformation, and metabolic lability benzylic position, iodine(I)/iodine(III) catalysis has been leveraged stereocontrolled generation selectively analogs. To augment current arsenal fluorocyclization reactions involving carboxylic...
Partially saturated, fluorine-containing rings are ubiquitous across the drug discovery spectrum. This capitalises upon biological significance of native structure and physicochemical advantages conferred by fluorination. Motivated aryl tetralins in bioactive small molecules, a reaction cascade has been validated to generate novel gem-difluorinated isosteres from 1,3-diaryl cyclobutanols single operation. Under Brønsted acidity catalysis conditions, an acid-catalysed unmasking/fluorination...
Abstract Cyclic β,β‐difluoro‐carbonyl compounds have a venerable history as drug discovery leads, but limitations in the synthesis arsenal continue to impede chemical space exploration. This challenge is particularly acute arena of fluorinated medium rings where installing difluoromethylene unit subtly alters ring conformation by expanding internal angle (∠C−CF 2 −C>∠C−CH −C): this provides handle modulate physicochemistry (e.g. p K ). To reconcile disparity, highly modular expansion has...
Simple α-(bromomethyl)styrenes can be processed to a variety of 1,1-difluorinated electrophilic building blocks via I(I)/I(III) catalysis. This inexpensive main group catalysis strategy employs p-TolI as an effective organocatalyst when combined with Selectfluor® and simple amine·HF complexes. Modulating Brønsted acidity enables simultaneous geminal vicinal difluorination occur, thereby providing platform generate multiply fluorinated scaffolds for further downstream derivatization. The...
We report a mild approach to the synthesis of difluoro(aryl)-λ3-iodanes (aryl-IF2 compounds) and tetrafluoro(aryl)-λ5-iodanes (aryl-IF4 using trichloroisocyanuric acid (TCICA) potassium fluoride (KF). Under these reaction conditions, selective access either I(iii)- or I(v)-derivatives is predictable based solely on substitution pattern iodoarene starting material. Moreover, discovery this TCICA/KF prompted detailed dynamic NMR, kinetic, computational, crystallographic studies relationship...
A main-group catalysis-based strategy to access 8-membered carbocycles via the direct carbofunctionalization of 2-phenethyl-substituted 1,3-dienes is disclosed. Through intervention an I(I)/I(III) catalysis cycle, synthesis densely functionalized, fluorinated benzocyclooctenes can be achieved in operationally simple manner. Modulating oxidation/activation regime, and external nucleophile, process has been extended unify challenging cyclization with formation allylic C-O, C-N, C-C bonds (>30...
Abstract Eine durch Iod (I/III) Katalyse ermöglichte Strategie zur Konstruktion eines enantioangereicherten fluorierten Isoster der Isopropylgruppe wird beschrieben. Die in situ Generierung einer chiralen ArIF 2 ‐Spezies ermöglicht die Difluorierung von leicht zugänglichen α‐CF 3 ‐Styrolen, um ein Stereozentrum mit den Substituenten F, CH F und CF aufzubauen (bis zu 95 %, >20:1 vicinale:geminale Difluorierung). Der Austausch des metabolisch labilen benzylischen Protons führt einem stark...
Abstract Der Erfolg von gesättigten, fluorierten Heterozyklen im Anwendungsbereich der modernen Arzneimittel bietet einen Anreiz für die Weiterentwicklung Hauptgruppenelement‐Katalyse. Motiviert durch Alleinstellung Isochromanen Spektrum bioaktiven kleinen Molekülen, wurden entsprechende fluorierte Analoga stereoselektiv mithilfe Iod(I)/Iod(III)‐Katalyse synthetisiert, unter anderem auch, um metabolische Labilität benzylischen Position zu umgehen. Die Acetaleinheit ist den anomeren Effekt...
Abstract Cyclic β,β‐difluoro‐carbonyl compounds have a venerable history as drug discovery leads, but limitations in the synthesis arsenal continue to impede chemical space exploration. This challenge is particularly acute arena of fluorinated medium rings where installing difluoromethylene unit subtly alters ring conformation by expanding internal angle (∠C−CF 2 −C>∠C−CH −C): this provides handle modulate physicochemistry (e.g. p K ). To reconcile disparity, highly modular expansion has...
Abstract A main‐group catalysis‐based strategy to access 8‐membered carbocycles via the direct carbofunctionalization of 2‐phenethyl‐substituted 1,3‐dienes is disclosed. Through intervention an I(I)/I(III) catalysis cycle, synthesis densely functionalized, fluorinated benzocyclooctenes can be achieved in operationally simple manner. Modulating oxidation/activation regime, and external nucleophile, process has been extended unify challenging cyclization with formation allylic C−O, C−N, C−C...
Abstract Joel Häfliger, Jahrgang 1995, ist zum Promovieren von der ETH Zürich an die Universität Münster gewechselt und überzeugt, für ihn einzig richtige Entscheidung getroffen zu haben.