A5037159175- Catalytic C–H Functionalization Methods
- Sulfur-Based Synthesis Techniques
- Synthesis and Catalytic Reactions
- Cyclopropane Reaction Mechanisms
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Catalytic Cross-Coupling Reactions
- Chemical Synthesis and Reactions
- Radical Photochemical Reactions
- Fluorine in Organic Chemistry
- Synthesis and Biological Activity
- N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
- Synthesis of Indole Derivatives
- Cancer therapeutics and mechanisms
- Synthesis of heterocyclic compounds
- Chemical Synthesis and Analysis
- Catalytic Alkyne Reactions
- Asymmetric Synthesis and Catalysis
- Asymmetric Hydrogenation and Catalysis
- Crystallography and molecular interactions
- Quinazolinone synthesis and applications
- Synthesis and Reactivity of Sulfur-Containing Compounds
- Organoboron and organosilicon chemistry
- Synthesis and bioactivity of alkaloids
- Phenothiazines and Benzothiazines Synthesis and Activities
Australian Regenerative Medicine Institute
2016-2025
Monash University
2015-2025
The University of Melbourne
2020-2023
Deakin University
2010-2019
RWTH Aachen University
2013-2015
A 'Cu'te couple: synthetically useful protocol for the preparation of N-alkynylated sulfoximines (yne sulfoximines) has been developed. The method involves a mild copper-catalyzed oxidative cross-coupling NH-sulfoximines and terminal alkynes (see scheme). corresponding N-acyl were also obtained selectively after acid-catalyzed hydrolysis yne sulfoximines. As service to our authors readers, this journal provides supporting information supplied by authors. Such materials are peer reviewed may...
A high-yielding method providing rapid access to new N-arylated sulfoximines has been developed. stoichiometric amount of copper facilitates the C–H activation 2-arylpyridines which then undergo oxidative C–N cross-couplings with various sulfoximine derivatives.
Abstract Over fifty years ago, the 1,2‐rearrangement of acylsilanes was first described by Adrian Brook and co‐workers. This rearrangement (now termed rearrangement) yields reactive silicon‐based singlet nucleophilic carbene (SNC) intermediates that participate in a variety chemical transformations including 1,2‐carbonyl addition, 1,4‐addition to electron‐deficient unsaturated bonds insertion into C−H O−H bonds. review aims cover historical literature recent advances with regard these...
Visible light induced singlet nucleophilic carbenes undergo rapid [2 + 1]-cycloaddition with tethered olefins to afford unique bicyclo[3.1.0]hexane and bicyclo[4.1.0]heptane scaffolds. This cyclopropanation process requires only visible irradiation proceed, circumventing the use of exogenous (photo)catalysts, sensitisers or additives showcases a vastly underexplored mode reactivity for in chemical synthesis. The discovery additional transformations including...
A method has been developed for the preparation of N-alkynylated sulfoximines involving copper-catalyzed decarboxylative coupling with aryl propiolic acids. range substituents on both sulfoximidoyl moiety and group acid were compatible this reaction process to afford a series sulfoximidoyl-functionalized alkynes.
Abstract Acylsilanes are known to undergo a 1,2‐silicon‐to‐oxygen migration under thermal or photochemical conditions form siloxycarbenes. However, there few reports regarding the application of siloxycarbenes in organic synthesis and surprisingly, their reaction with CC double triple bonds remains virtually unexplored. To facilitate such study, previously inaccessible aromatic acylsilanes containing an ortho‐ tethered bond were identified as suitable substrates. access these key...
Abstract A method to access α‐thioaryl ketones and esters employing copper acetate (hydrate) as catalyst readily accessible diaryl disulfides β‐diketones (or β‐keto esters) has been developed. Both alkyl‐ aryl‐substituted carbonyl compounds can be prepared. magnified image
Investigations into C-H amidation reactions catalysed by cationic half-sandwich d6 metal complexes revealed that the indenyl-derived catalyst [Ind*RhCl2 ]2 significantly accelerated directed ortho of benzoyl silanes using 1,4,2-dioxazol-5-ones. Ring slippage involving a haptotropic η5 to η3 rearrangement indenyl complex proposedly enables ligand substitution at centre proceed via associative, rather than dissociative pathways, leading significant rate and yield enhancements. Intriguingly,...
Abstract An oxidative cross‐coupling reaction between aldehydes and sulfoximines involving dual CH/NH functionalization has been developed. This process is facilitated by a simple copper catalyst (1 mol% loading) tert ‐butyl hydroperoxide (TBHP) as the oxidant proceeds under mild conditions to afford series of valuable N ‐acylated sulfoximine derivatives in excellent yields.
An investigation into the reactivity profile of N-halogenated sulfoximines has led to development a new method for synthesis N-aroylated sulfoximines. This protocol involves manganese oxide promoted C-H activation methyl arenes form an aroyl intermediate which then reacts readily with N-chlorosulfoximines series valuable sulfoximine derivatives in high yields.
Siloxy carbenes, formed thermally or photochemically from acyl silanes via a 1,2-Brook rearrangement, are intriguing reactive intermediates that partake in range of chemical reactions. To gain further insight into the properties this class thermodynamic stabilities series known siloxy carbenes were explored on basis hydrogenation enthalpies. Calculations conducted at B3LYP-D3(BJ) level (using dispersion-corrected DFT) (X–C–OSiR3, singlet and triplet state), oxocarbenium ions (X–CH–OSiR3+),...
Siloxycarbenes induced via the visible light irradiation of acylsilanes undergo highly efficient “photo-click” chemistry reactions with electron deficient ketones. This process requires no reagents other than light, proceeds high efficiency and is tolerant a wide range functional groups. Pyruvate esters, thioesters, amides, nitriles phosphonates were all suitable electrophiles including those tethered to complex drug or biomolecule scaffolds. The was achieved on larger scale using both batch...
A library of potent WEE1 kinase inhibitors was synthesized based on the discontinued frontrunner clinical candidate AZD1775 (1), many which were more selective for over an undesirable off-target 1, PLK1. When tested against patient-derived organoids (PDOs) grown from TP53-mutated colorectal cancer (CRC) peritoneal metastases, 34 (IC50 value 62 nM) exhibited stronger efficacy than 1 120 and best-in-class ZN-c3 127 nM). Against primary CRC PDOs with TP53-WT, significantly enhanced DNA damage,...
Light-induced Brook rearrangements of acylsilanes facilitate silylacylation reactions electron-deficient internal alkynes. A wide range aromatic substituents on the acylsilane aryl group are tolerated, affording a series functionalized enonyl silanes. The presence electron-withdrawing alkyne is crucial for success addition process.
Singlet nucleophilic carbenes (SNCs) containing only one heteroatom donor remain underutilized in chemical synthesis. We recently discovered that visible-light-induced SNC intermediates can be trapped by fluorinated ketones via 1,2-carbonyl addition to afford benzoin-type products. This discovery represents a rare example of reacting with and delivers an efficient, user-friendly, scalable process for accessing tertiary alcohol derivatives driven light circumventing the use exogenous...
CH(3)CN and O(2) do the trick! A copper-mediated direct oxidative cross-coupling of 2-(het)aryl-1,3,4-oxadiazoles with polyhaloarenes under mild reaction conditions has been developed (see scheme). The process provides a concise access to biaryl structures containing polyhaloarenes, which are interest in fields pharmaceuticals functional materials. Acetonitrile oxygen play crucial roles.
To assess the potential of N-alkynylated sulfoximines as new (chiral) reagents for organic synthesis, their reactivity profile in numerous synthetic processes is under investigation. When reacted with ketenes, alkynylated-sulfoximines undergo a [2 + 2]-cycloaddition process to afford sulfoximine-functionalized cyclobutenones excellent yields.
A high-throughput screen for inhibitors of the histone acetyltransferase, KAT6A, led to identification an aryl sulfonohydrazide derivative (CTX-0124143) that inhibited KAT6A with IC50 1.0 μM. Elaboration structure-activity relationship and medicinal chemistry optimization discovery WM-8014 (97), a highly potent inhibitor (IC50 = 0.008 μM). competes acetyl-CoA (Ac-CoA), X-ray crystallographic analysis demonstrated binding Ac-CoA site. Through inhibition activity, induces cellular senescence...
A simple and efficient palladium-catalyzed domino reaction for the synthesis of a series C1-substituted tetrahydro-beta-carbolines is described. This process involves Heck at indole 2-position halogenated tryptamine precursor, followed by intramolecular aza-Michael addition.
Ein präparativ nützliches Protokoll für die Synthese von N-alkinylierten Sulfoximinen (Insulfoximine) wurde entwickelt. Die Methode umfasst eine milde Kupfer-katalysierte oxidative Kreuzkupplung NH-Sulfoximinen mit terminalen Alkinen (siehe Schema). Säurekatalysierte Hydrolyse der Insulfoximine führte selektiv zu den entsprechenden N-Acylsulfoximinen.
Palladium-catalyzed domino Heck-aza-Michael reactions for the synthesis of a series C1-substituted tetrahydro-β-carbolines, tetrahydroisoquinolines and isoindolines are described. The process involves initial intermolecular Heck reaction an aryl bromide with electron deficient alkene, followed by intramolecular aza-Michael to form new N-heterocycle in high yield.
Abstract Acylsilanes are known to undergo a 1,2‐silicon‐to‐oxygen migration under thermal or photochemical conditions form siloxycarbenes. However, there few reports regarding the application of siloxycarbenes in organic synthesis and surprisingly, their reaction with CC double triple bonds remains virtually unexplored. To facilitate such study, previously inaccessible aromatic acylsilanes containing an ortho‐ tethered bond were identified as suitable substrates. access these key...
A new method for the regioselective and stereoselective iodoacyloxylation of alkynes has been developed. This protocol utilizes a combination an iodobenzene dicarboxylate iodine to functionalize series activated unactivated in entirely selective predictable fashion. The resultant iodo-enol esters were subsequently coupled with boronic acids afford tetrasubstituted alkene derivatives, which could be further converted corresponding 1,1-disubstituted acetophenone.