A5080368713- Catalytic C–H Functionalization Methods
- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Asymmetric Hydrogenation and Catalysis
- Synthesis and Catalytic Reactions
- Axial and Atropisomeric Chirality Synthesis
- Catalytic Cross-Coupling Reactions
- Asymmetric Synthesis and Catalysis
- Molecular spectroscopy and chirality
- Radical Photochemical Reactions
- Sulfur-Based Synthesis Techniques
- Oxidative Organic Chemistry Reactions
- Cyclopropane Reaction Mechanisms
- Alkaloids: synthesis and pharmacology
- Chemical synthesis and alkaloids
- Synthetic Organic Chemistry Methods
- Crystallography and molecular interactions
- Cyclization and Aryne Chemistry
- Catalytic Alkyne Reactions
- Chemical Synthesis and Analysis
- Organoboron and organosilicon chemistry
- Chemical Synthesis and Reactions
- Fluorine in Organic Chemistry
- Vanadium and Halogenation Chemistry
- Chemistry and Chemical Engineering
University of Würzburg
2023-2025
Université de Haute-Alsace
2018-2024
Centre National de la Recherche Scientifique
2015-2024
Université de Strasbourg
2015-2024
Laboratoire d'innovation moléculaire et applications
2011-2024
National Renewable Energy Laboratory
2024
University of Colorado Boulder
2024
Leibniz-Institute for New Materials
2024
Environmental Energy & Engineering
2024
The University of Adelaide
2024
The use of coordinating moieties as directing groups for the functionalization aromatic C-H bonds has become an established tool to enhance reactivity and induce regioselectivity. Nevertheless, with regard synthetic applicability activation, there is a growing interest in transformations which group can be fully abandoned, thus allowing direct simple benzene derivatives. However, this approach requires disclosure new strategies achieve control selectivity. In review, recent advances emerging...
Abstract Der Einsatz von koordinierenden Gruppen als dirigierende ist eine zuverlässige Methode zur Kontrolle Reaktivität und Selektivität bei der Aktivierung Aryl‐C‐H‐Bindungen. Im Hinblick auf die Anwendbarkeit C‐H‐Aktivierungen in Synthese besteht derzeit ein großes Interesse daran, Reaktionen zu entwickeln, denen völlig verzichtet werden kann somit Funktionalisierung einfacher Benzolderivate möglich wird. Dieser Ansatz erfordert jedoch neue Strategien Reaktivitäts‐...
We report a uniquely high-yielding, general, and practical ortho bromination iodination reaction of different classes aromatic compounds. This occurs by Rh(III)-catalyzed C-H bond activation methodology is therefore the first example application this cationic catalyst for C-Br C-I formation.
Abstract A mild and robust direct CH functionalization strategy has been applied to the synthesis of axially chiral biaryls. Such an efficient stereoselective transformation occurs through original dynamic kinetic resolution pathway enabling conversion diastereomeric mixtures non‐prefunctionalized substrates into atropisomerically pure, highly substituted biaryl scaffolds. The main feature this is use enantiopure sulfoxide as both auxiliary traceless directing group. potential newly...
Directed, undirected! Rhodium(III)-catalyzed double CH bond activation (one directed, one undirected) provides an efficient route to biaryls (see scheme; DG=directing group). Significant kinetic isotope effects for both reaction partners and H/D scrambling between them are interesting experimental findings. While the mechanism is still unclear, a rhodium(V) species invoked in catalytic cycle.
Abstract A “niche” topic in the past decade, asymmetric CH bond activation has been attracting growing interest over last few years. Particularly significant advances have achieved field of direct, stereoselective transformations C(sp 2 )H bonds. This Concept article intends to showcase different types reactions, emphasising both nature stereo‐discriminating step and variability valuable scaffolds that could be rapidly constructed by means such strategies.
Fluorinated solvents like 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and trifluoroethanol (TFE) have recently emerged as a remarkable synthetic hint allowing challenging C–H activation reactions.
Atropoisomeric (hetero)biaryls are scaffolds with increasing importance in the pharmaceutical and agrochemical industries. Although it is most obvious disconnection to construct such compounds, direct enantioselective C–H arylation through concomitant induction of chiral information remains extremely challenging uncommon. Herein, unprecedented earth-abundant 3d-metal-catalyzed atroposelective reported, furnishing rare atropoisomeric C2-arylated indoles. Kinetic studies DFT computation...
C6Brsix & drugs! C6Br6 can be used as the cooxidant/catalyst modifier for [RhIIICp*]-catalyzed (Cp*=C5Me5) dehydrogenative cross-coupling of benzamides with simple benzene derivatives (see scheme, DG=directing group). Similarly, heterocycles coupled and druglike structures formed. Mechanistic studies suggest a unique multiple role Cu(OAc)2/C6Br6 system nonchelate-assisted CH activation rate-determing step. Detailed facts importance to specialist readers are published "Supporting...
Abstract Herein we disclose the synthesis of original chiral scaffolds— ortho ‐orientated terphenyls presenting two atropisomeric Ar–Ar axes. These unusual structures were built up by using C−H activation approach, and remarkably, both axes controlled with excellent stereoselectivity in a single transformation. During reaction, not only does atroposelective functionalization biaryl precursor occur to establish one stereogenic axis, but an unprecedented atropo‐stereoselective arylation also...
Abstract Molekulare Synthese basiert größtenteils auf zeit‐ und arbeitsintensiven Präfunktionalisierungsstrategien. Demgegenüber bietet die C‐H‐Aktivierung ein leistungsstarkes Hilfsmittel, das ohne lange Synthesen präfunktionalisierter Substrate auskommt großes Potenzial für z. B. Wirkstoffentwicklung, pharmazeutische Industrie, Materialwissenschaften von Pflanzenschutzmitteln hat. Die enantioselektive Funktionalisierung omnipräsenter C‐H‐Bindungen hat sich zu einer etablierten Methode...
N-C axially chiral compounds have emerged recently as appealing motifs for drug design. However, the enantioselective synthesis of such molecules is still poorly developed and surprisingly no metal-catalyzed atroposelective N-arylations been described. Herein, we disclose an unprecedented Cu-catalyzed coupling that proceeds at room temperature. Such mild reaction conditions, which are a crucial parameter atropostability newly generated products, operative thanks to use hypervalent iodine...
This Review recaps the achievements in field of metal-catalyzed asymmetric direct hydrogenation nonactivated and activated imines. A summary reported catalytic systems with corresponding reactivity, selectivity, limitations is given including a discussion about effects some reaction conditions on enantioselectivity imine hydrogenation. An analysis proposed mechanisms discussed.
ConspectusThe expanding applications of atropisomeric compounds combined with the growing diversity such chiral molecules translate into an urgent need for innovative synthetic strategies allowing their rapid, efficient, and sustainable synthesis. Recently, C-H activation approach has provided new opportunities synthesizing axially compounds. The two complementary approaches implementation methodology toward synthesis imply either ortho-functionalization preexisting prochiral or...
Abstract The assembly of chiral molecules with multiple stereogenic elements is challenging, and, despite indisputable advances, largely limited to toxic, cost-intensive and precious metal catalysts. In sharp contrast, we herein disclose a versatile C–H alkylation using non-toxic, low-cost iron catalyst for the synthesis substituted indoles two elements. key achieving excellent diastereo- enantioselectivity was substitution on N -heterocyclic carbene ligand providing steric hindrance extra...