ORCID Profile
0000-0002-0757-9970
Current Organisation
University of New South Wales
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Research Topics
In Research Link Australia (RLA), "Research Topics" refer to ANZSRC FOR and SEO codes. These topics are either sourced from ANZSRC FOR and SEO codes listed in researchers' related grants or generated by a large language model (LLM) based on their publications.
Top 5 Research Topics
ANZSRC Field of Research (FoR)
Organic Chemistry | Organic Chemical Synthesis | Physical Organic Chemistry | Catalysis and Mechanisms of Reactions | Macromolecular and Materials Chemistry | Synthesis of Materials | Organic Green Chemistry | Colloid and Surface Chemistry | Analytical Spectrometry | Nanochemistry and Supramolecular Chemistry | Physical Chemistry (Incl. Structural) | Structural Chemistry and Spectroscopy | Structural Biology (incl. Macromolecular Modelling) | Sociology and Social Studies of Science and Technology
ANZSRC Socio-Economic Objective (SEO)
Expanding Knowledge in the Chemical Sciences | Expanding Knowledge in the Biological Sciences | Human Pharmaceutical Treatments (e.g. Antibiotics) | Workforce Transition and Employment | Expanding Knowledge in the Physical Sciences | Organic Industrial Chemicals (excl. Resins, Rubber and Plastics) |
Related Links
Publications
The Resurgence of the Highly Ylidic N-Heterocyclic Olefins as a New Class of Organocatalysts
Publisher: Wiley
Date: 26-11-2015
Abstract: In recent decades, N-heterocyclic carbenes have become established as a prevalent family of organocatalysts. N-Heterocyclic olefins, the alkylidene derivatives of N-heterocyclic carbenes, have recently also emerged as efficient promoters for CO2 fixation and polymerization reactions. Their extraordinarily strong Lewis/Brønsted basicity suggests great potential as a new class of organocatalysts for a broad range of reactions in synthetic chemistry.
Tropylium tetrafluoroborate promoted hydroboration of nitriles, imines and amides
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D2GC01905A
Abstract: A new organocatalytic approach to reduce nitriles, imines or amides with pinacolborane to amines is reported.
Tropylium-promoted Ritter reactions
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D1CC02947A
Abstract: The tropylium ion serves as an excellent and environmentally-benign catalyst for the Ritter reaction.
Carbothermal synthesis of nano-sized tungsten carbide catalyst
Publisher: Elsevier
Date: 2006
Immobilized Carbodiimide Assisted Flow Combinatorial Protocol to Facilitate Amide Coupling and Lactamization
Publisher: American Chemical Society (ACS)
Date: 13-04-2020
Unusual Alternating Crystallization-Induced Emission Enhancement Behavior in Nonconjugated ω-Phenylalkyl Tropylium Salts
Publisher: American Chemical Society (ACS)
Date: 22-11-2021
DOI: 10.1021/JACS.1C10038
Norcaradiene Synthesis via Visible-Light-Mediated Cyclopropanation Reactions of Arenes
Publisher: American Chemical Society (ACS)
Date: 16-10-2019
DOI: 10.1021/ACS.ORGLETT.9B03453
Abstract: Cyclopropanation reactions of carbenes with arenes provide a straightforward pathway to norcaradienes or cycloheptatrienes. This reaction normally requires harsh reaction conditions or transition-metal catalysts. In this report, we describe the metal-free visible-light photolysis of aryl diazoacetates in aromatic solvents, which provides access to the norcaradiene ring system in a highly regio- and stereoselective manner. The mild reaction conditions of this approach also allow chemoselective cyclopropanation of substituted arenes without competing C-H functionalization reactions.
Formal Electrophilic Phenylation Reaction with Tropylium Ion
Publisher: American Chemical Society (ACS)
Date: 09-06-2021
DOI: 10.26434/CHEMRXIV.14747430.V1
Abstract: Arylation reaction is an important transformation in synthetic chemistry as aryl building blocks are ubiquitous in valuable organic frameworks. Traditionally, this type of reaction has been carried out either via biaryl coupling reactions or with the use of reactive intermediates such as arynes or aryl radicals. Direct electrophilic arylation reactions have been rarely reported in literature, as the required arenium building blocks are often unstable or inaccessible. To develop a new strategy for such transformation, we herein introduce the development of a formal phenylation reaction, which proceeds via an electrophilic cycloheptatrienylation with tropylium ion, followed by an oxidative ring-contraction.
A novel aromatic carbocation-based coupling reagent for esterification and amidation reactions
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C4CC09539A
Abstract: Driven by aromatization : a novel tropylium-based coupling reagent has been developed to facilitate nucleophilic coupling reactions of carboxylic acids.
Halide Anion Triggered Reactions of Michael Acceptors with Tropylium Ion
Publisher: Wiley
Date: 04-12-2019
Iodonium-Catalyzed Carbonyl–Olefin Metathesis Reactions
Publisher: Georg Thieme Verlag KG
Date: 10-2019
Abstract: The carbonyl–olefin metathesis reaction has become increasingly important in organic synthesis due to its versatility in functional group interconversion chemistry. Recent developments in the field have identified a number of transition-metal and organic Lewis acids as effective catalysts for this reaction. Herein, we report the use of simple organic compounds such as N-iodosuccinimide or iodine monochloride to catalyze the carbonyl–olefin metathesis process under mild reaction conditions. This work broadens the scope of this chemical transformation to include iodonium sources as simple and practical catalysts.
Development and Applications of Transesterification Reactions Catalyzed by N-Heterocyclic Olefins
Publisher: American Chemical Society (ACS)
Date: 26-04-2016
DOI: 10.1021/ACS.ORGLETT.6B00835
Abstract: A novel method to utilize N-heterocyclic olefins (NHOs), the alkylidene derivatives of N-heterocycic carbenes, as organocatalysts to promote transesterification reactions has been developed. Because of their strong Brønsted/Lewis basicity, NHOs can enhance the nucleophilicity of alcohols for their acylation reactions with carboxylic esters. This transformation can be employed in industrially relevant processes such as the production of biodiesel, the depolymerization of polyethylene terephthalate (PET) from plastic bottles for recycling purposes, and the ring-opening polymerization of cyclic esters to form biodegradable polymers such as polylactide (PLA) and polycaprolactone (PCL).
Promotion of Organic Reactions by Non‐Benzenoid Carbocyclic Aromatic Ions
Publisher: Wiley
Date: 13-12-2016
Abstract: The first three primary members of the non-benzenoid carbocyclic aromatic ion family, namely cyclopropenium, cyclopentadienide, and cycloheptatrienium (tropylium) ions, have planar cyclic structures with (4n+2)π electrons in fully conjugated systems. They fulfill Hückel's rule for aromaticity and hence possess extraordinary stability. Since the historic discovery of tropylium bromide in the late 19th Century, these non-benzenoid aromatic ions have attracted a lot of attention because of their unique combination of stability and reactivity. The charge on the aromatic ions makes them more prone to nucleophilic/electrophilic reactions than the neutral benzenoid counterparts. Within the last seven years, there has been a large number of investigations in utilizing aromatic ions to mediate organic reactions. This Review highlights these recent developments and discusses the potential of aromatic ions in promoting synthetically useful organic transformations.
Catalytic Synthesis of Trifluoromethyl Cyclopropenes and Oligo‐Cyclopropenes
Publisher: Wiley
Date: 20-01-2020
Multi C−H Functionalization Reactions of Carbazole Heterocycles via Gold‐Catalyzed Carbene Transfer Reactions
Publisher: Wiley
Date: 12-01-2021
Abstract: Herein we describe a multiple C−H functionalization reaction of carbazole heterocycles with diazoalkanes. We show that gold catalysts play a distinct role in enabling a multiple C−H functionalization reaction to introduce up to six carbene fragments onto molecules containing multiple carbazole units or to link multiple carbazole units into a single molecule. A one‐pot stepwise approach enables the introduction of two different carbene fragments to allow orthogonal deprotection and straightforward derivatization.
Tropolonate Salts as Acyl Transfer Catalysts for Esterification Reactions under Thermal and Photochemical Conditions
Publisher: American Chemical Society (ACS)
Date: 20-08-2020
DOI: 10.26434/CHEMRXIV.12824921.V1
Abstract: Acyl transfer catalysis is a frequently used tool to promote the formation of carboxylic acid derivatives, which are important synthetic precursors and target compounds in organic synthesis. However, there have been only a few structural motifs known to efficiently catalyze the acyl transfer reaction. Herein we introduce a new acyl transfer catalytic paradigm based on the tropolone framework. We show that tropolonate salts, due to their strong nucleophilicity and photochemical activity, can promote the coupling reaction between alcohols and carboxylic acid anhydrides or chlorides to give the products with excellent efficiency under thermal or blue light-photochemical conditions. Kinetic studies and density functional theory (DFT) calculations suggest interesting mechanistic insights for reactions promoted by this new acyl transfer catalytic system.
Recent Synthetic Strategies to Access Seven-Membered Carbocycles in Natural Product Synthesis
Publisher: Georg Thieme Verlag KG
Date: 04-03-2013
Synthesis of Tertiary Amines by Direct Brønsted Acid Catalyzed Reductive Amination
Publisher: American Chemical Society (ACS)
Date: 21-04-2020
DOI: 10.26434/CHEMRXIV.12155394.V1
Abstract: Tertiary amines are ubiquitous and valuable compounds in synthetic chemistry, with a wide range of applications in organocatalysis, organometallic complexes, biological processes and pharmaceutical chemistry. One of the most frequently used pathways to synthesize tertiary amines is the reductive amination reaction of carbonyl compounds. Despite developments of numerous new reductive amination methods in the past decades, this reaction generally requires non-atom-economic processes with harsh conditions and toxic transition-metal catalysts. Herein we report simple yet practical protocols using triflic acid as catalyst to efficiently promote direct reductive amination reactions of carbonyl compounds on a broad ranges of substrates. Applications of this new method to generate valuable heterocyclic frameworks and polyamines are also included.
Selective binding and release of aspirin by an encapsulating receptor
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/C0CC00422G
Abstract: The selective binding of aspirin deep inside superbowl synthetic hosts is reported. Evidence for a two-point binding mode of the drug by the host is presented. Both the strength of aspirin binding and the rate of its release are manipulated by altering the substituents about the host's aperture.
NHC‐Catalyzed Metathesis and Phosphorylation Reactions of Disulfides: Development and Mechanistic Insights
Publisher: Wiley
Date: 07-04-2017
Abstract: The development of efficient methods for the metathesis and phosphorylation reactions of disulfide compounds is of widespread interest due to their important synthetic utility in polymer, biological, medicinal and agricultural chemistry. Herein, we demonstrate the use of N-heterocyclic carbenes (NHCs) as versatile organocatalysts to promote these challenging reactions under mild conditions. This metal- and oxidant-free protocol is operationally simple with very short reaction times. The interplay between the nucleophilicity and basicity of NHCs in these reactions were also elucidated by NMR studies and high-level ab initio calculations.
A Universal Organocatalyst for Selective Mono-, Di-, and Triboration of Terminal Alkynes
Publisher: American Chemical Society (ACS)
Date: 06-2023
Iodine Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights
Publisher: American Chemical Society (ACS)
Date: 06-07-2020
DOI: 10.26434/CHEMRXIV.12607529.V1
Abstract: Substituted pyrans and furans are core structures found in a wide variety of natural products and biologically-active compounds. Herein, we report a practical and mild catalytic method for the synthesis of substituted pyrans and furans using molecular iodine, a simple and inexpensive catalyst. The method described herein is performed in solvent-free conditions in ambient temperature and atmosphere, thus offering a facile and green alternative to currently available reaction protocols. A combination of experimental studies and high‐level DFT calculations revealed interesting mechanistic insights of this seemingly simple reaction.
Elucidation of structures and lithium environments for an organo-sulfur cathode
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9CP03057C
Abstract: In-depth analysis of solid state NMR, XRD and X-ray absorption spectroscopy data is used to detail the function of an organo-sulfur cathode.
Toward Homogeneous Brønsted-Acid-Catalyzed Intramolecular Carbonyl–Olefin Metathesis Reactions
Publisher: American Chemical Society (ACS)
Date: 27-09-2022
DOI: 10.1021/ACS.ORGLETT.2C03099
Abstract: The carbonyl-olefin metathesis (COM) reaction is an attractive approach for the formation of a new carbon-carbon double bond from a carbonyl precursor. In principle, this reaction can be promoted by the activation of the carbonyl group with a Brønsted acid catalyst however, it is often complicated as a result of unwanted side reactions under acidic conditions. Thus, there have been only a very few ex les of Brønsted-acid-catalyzed COM reactions, all of which required specially designed setups. Herein, we report a new practical homogeneous Brønsted-acid-catalyzed protocol using nitromethane, a readily available solvent, to promote intramolecular ring-closing COM reactions.
Carbocation-Catalyzed Intramolecular and Intermolecular Carbonyl-Alkyne Metathesis Reactions
Publisher: American Chemical Society (ACS)
Date: 07-02-2023
Organosuperbase-Catalyzed 1,1-Diboration of Alkynes
Publisher: American Chemical Society (ACS)
Date: 28-09-2022
Chiral quaternary phosphonium salts: a new class of organocatalysts
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2OB25823D
Abstract: Phase-transfer catalysis has widely been used as a prime synthetic tool for both laboratory and industrial processes. During the last twenty years, asymmetric phase-transfer catalysis using chiral organocatalysts has attracted widespread interest. However, the scope of chiral phase-transfer catalysis has been limited mostly to the quaternary ammonium salts. As an emerging area, the recent developments in the application of quaternary phosphonium salts as chiral phase-transfer catalysts are discussed in this article.
Ring Contraction of Tropylium Ions into Benzenoid Derivatives
Publisher: American Chemical Society (ACS)
Date: 24-03-2022
DOI: 10.1021/ACS.ORGLETT.2C00663
Abstract: We report a method to convert substituted tropylium ions into benzenoid derivatives.
Tropylium-promoted prenylation reactions of phenols in continuous flow
Publisher: Springer Science and Business Media LLC
Date: 17-02-2020
Extraction of gallium from Bayer liquor using extractant produced from cashew nutshell liquid
Publisher: Elsevier BV
Date: 08-2015
Efficient phosphine-mediated formal C(sp3)-C(sp3) coupling reactions of alkyl halides in batch and flow
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7CC02033C
Abstract: The Wittig-type chemical procedure is adapted to efficiently facilitate alkyl–alkyl coupling reactions in batch and flow.
Tropylium-Promoted Oxidative Functionalization of Tetrahydroisoquinolines
Publisher: American Chemical Society (ACS)
Date: 03-01-2018
Abstract: Structural modification of the tetrahydroisoquinoline (THIQ) framework is of significant interest to organic chemists due to its central role in heterocyclic and medicinal chemistry. Here we demonstrate an efficient metal-free method for the oxidative functionalization of THIQs at the C1 position, which is amenable to a erse range of C-C coupling reactions. These reactions proceed through a hydride abstraction involving the tropylium ion followed by quenching the generated iminium intermediates with nucleophiles to afford THIQ derivatives with excellent efficiencies and interesting selectivities.
Tropylium salts as efficient organic Lewis acid catalysts for acetalization and transacetalization reactions in batch and flow
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7GC01519D
Abstract: Tropylium salts were reported as organic-Lewis acids to efficiently catalyze acetalization reactions in batch and flow.
Simple Synthetic Receptors for Aspirin
Publisher: Wiley
Date: 16-10-2014
Abstract: Shallow methylene-bridged cavitands appended with simple H-bond donor/acceptor groups are shown to bind aspirin. The structural features needed in a synthetic receptor for aspirin binding are defined.
Gold‐catalyzed C−H Functionalization of Phenothiazines with Aryldiazoacetates
Publisher: Wiley
Date: 12-11-2020
Tetrabenzo[5.7]fulvalene: a forgotten aggregation induced-emission luminogen
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9CC06289K
Abstract: Tetrabenzo[5.7]fulvalene has been proven to be an outstanding aggregation-induced emission fluorophore.
Aromatic Cation Activation: Nucleophilic Substitution of Alcohols and Carboxylic Acids
Publisher: American Chemical Society (ACS)
Date: 06-03-2014
DOI: 10.1021/OL5003972
Abstract: A new method for the nucleophilic substitution of alcohols and carboxylic acids using aromatic tropylium cation activation has been developed. This article reports the use of chloro tropylium chloride for the rapid generation of alkyl halides and acyl chlorides under very mild reaction conditions. It demonstrates, for the first time, the synthetic potential of tropylium cations in promoting chemical transformations.
Tropylium Salt Promoted Hydroboration Reactions: Mechanistic Insights via Experimental and Computational Studies
Publisher: American Chemical Society (ACS)
Date: 19-01-2021
DOI: 10.26434/CHEMRXIV.13599329.V1
Abstract: Abstract: Hydroboration reaction of alkynes is one of the most synthetically powerful tools to access organoboron compounds, versatile precursors for cross coupling chemistry. This type of reaction has traditionally been mediated by transition metal or main group catalysts. Herein, we report a novel method using tropylium salts, typically known as organic oxidants and Lewis acids, to efficiently promote the hydroboration reaction of alkynes. A broad range of vinylboranes can be easily accessed via this metal-free protocol. Similar hydroboration reactions of alkenes and epoxides can also be efficiently catalyzed by the same tropylium catalysts. Experimental studies and DFT calculations suggested that the reaction follows an uncommon mechanistic paradigm, which is triggered by a hydride abstraction of pinacolborane with tropylium ion. This is followed by a series of in situ counterion-activated substituent exchanges to generate boron intermediates that promote the hydroboration reaction.
Mechanistic implications of Li–S cell function through modification of organo-sulfur cathode architectures
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D1CP01838H
Abstract: Solid-state NMR reveals unique correlations between lithium environments within an organo-sulfur cathode, providing key insight on the interfacial processes involved when using inverse vulcanised copolymers in lithium-sulfur cells.
Halide Anion Triggered Reactions of Michael Acceptors with Tropylium Ion
Publisher: Wiley
Date: 04-12-2020
Abstract: Tropylium bromide undergoes noncatalyzed, regioselective additions to a large variety of Michael acceptors. In this way, acrylic esters are converted into β-bromo-α-cycloheptatrienylpropionic esters. The reactions are interpreted as nucleophilic attack of bromide ions at the electron-deficient olefins and the approach of the tropylium ion to the incipient carbanion. Quantum chemical calculations were performed to elucidate the analogy to the amine- or phosphine-catalyzed Rauhut-Currier reactions. Subsequent synthetic transformations of the bromo-cycloheptatrienylated adducts are reported.
Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights
Publisher: American Chemical Society (ACS)
Date: 28-05-2021
Hydrogen Bonding Networks Enable Brønsted Acid‐Catalyzed Carbonyl‐Olefin Metathesis**
Publisher: Wiley
Date: 10-02-2022
Abstract: Synthetic chemists have learned to mimic nature in using hydrogen bonds and other weak interactions to dictate the spatial arrangement of reaction substrates and to stabilize transition states to enable highly efficient and selective reactions. The activation of a catalyst molecule itself by hydrogen‐bonding networks, in order to enhance its catalytic activity to achieve a desired reaction outcome, is less explored in organic synthesis, despite being a commonly found phenomenon in nature. Herein, we show our investigation into this underexplored area by studying the promotion of carbonyl‐olefin metathesis reactions by hydrogen‐bonding‐assisted Brønsted acid catalysis, using hexafluoroisopropanol (HFIP) solvent in combination with para ‐toluenesulfonic acid (pTSA). Our experimental and computational mechanistic studies reveal not only an interesting role of HFIP solvent in assisting pTSA Brønsted acid catalyst, but also insightful knowledge about the current limitations of the carbonyl‐olefin metathesis reaction.
N-Heterocyclic Olefin Catalyzed Silylation and Hydrosilylation Reactions of Hydroxyl and Carbonyl Compounds
Publisher: American Chemical Society (ACS)
Date: 23-02-2017
DOI: 10.1021/ACS.ORGLETT.7B00306
Abstract: N-Heterocyclic olefins (NHOs), the alkylidene derivatives of N-heterocyclic carbenes (NHCs), have recently emerged as a new family of promising organocatalysts with strong nucleophilicity and Brønsted basicity. The development of a novel method is shown using NHOs as efficient promoters for the direct dehydrogenative silylation of alcohols or hydrosilylation of carbonyl compounds. Preliminary results of the first NHO-promoted asymmetric synthesis are also discussed.
Tropylium-Catalyzed O–H Insertion Reactions of Diazoalkanes with Carboxylic Acids
Publisher: American Chemical Society (ACS)
Date: 05-01-2021
Stimuli‐Responsive Organic Dyes with Tropylium Chromophore
Publisher: Wiley
Date: 03-07-2018
Abstract: Tropylium ions possess an interesting combination of structural stability and chemical reactivity due to its Hückel aromaticity and its positively charged polyene nature, respectively. Herein we exploit the chemical versatility and unique structural properties of the tropylium ion to derive a family of novel push-pull organic dyes with strong absorption in the visible range via simple and practical synthetic protocols. These stable organic dyes are highly stimuli-responsive, as demonstrated by their sensitivity towards solvent, pH change, redox reaction, Lewis base and counterion, which marks them as potentially useful compounds for opto-electronic applications.
Dynamic adsorption of a gemini surfactant at the air/water interface
Publisher: Elsevier BV
Date: 10-2015
Synthesis of tertiary amines by direct Brønsted acid catalyzed reductive amination
Publisher: Royal Society of Chemistry (RSC)
Date: 2020
DOI: 10.1039/D0CC02955F
Abstract: Triflic acid efficiently promotes the reductive amination reactions of carbonyl compounds on a broad range of substrates.
Tropylium Ion Catalyzes Hydration Reactions of Alkynes
Publisher: Wiley
Date: 14-06-2018
Photochemical O–H Functionalization of Aryldiazoacetates with Phenols via Proton Transfer
Publisher: American Chemical Society (ACS)
Date: 31-08-2020
Intramolecular Oxidative Heck Cyclization: a Novel Pathway to Cyclopentenones
Publisher: CSIRO Publishing
Date: 2008
DOI: 10.1071/CH08026
Structural evolution of alumina supported Mo–W carbide nanoparticles synthesized by precipitation from homogeneous solution
Publisher: Elsevier BV
Date: 2005
Corey–Chaykovsky Reactions of Nitro Styrenes Enable cis-Configured Trifluoromethyl Cyclopropanes
Publisher: American Chemical Society (ACS)
Date: 17-07-2017
Abstract: Trifluoromethyl-substituted cyclopropanes are an attractive family of building blocks for the construction of pharmaceutical and agrochemical agents. This work demonstrated the utilization of fluorinated sulfur ylides as versatile reagents for Corey-Chaykovsky cyclopropanation reactions of nitro styrenes. This protocol favored the synthesis of cis-configured trifluoromethyl cyclopropanes for a broad range of substrates with excellent yields and good diastereoselectivities.
Guest Binding Drives Reversible Atropisomerism in Cavitand Hosts
Publisher: Wiley
Date: 08-06-2009
Abstract: Guest-love-ometer: The equilibrium inside-outside atropisomeric ratio of ortho-substituted phenyl cavitands shows a strong solvent dependence. The competition between the ortho-substituent and the solvent guest for the bowl cavity leads to a sensitive system for the measurement of relative guest binding affinities.
An efficient method for retro-Claisen-type C–C bond cleavage of diketones with tropylium catalyst
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8CC07329E
Abstract: We report a new convenient and efficient method utilizing the tropylium ion as a mild and environmentally friendly organocatalyst to mediate retro -Claisen-type reactions.
Tropolonate Salts as Acyl-Transfer Catalysts under Thermal and Photochemical Conditions: Reaction Scope and Mechanistic Insights
Publisher: American Chemical Society (ACS)
Date: 15-10-2020
N-Heterocyclic olefins as efficient phase-transfer catalysts for base-promoted alkylation reactions
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6CC03771B
Abstract: N-Heterocyclic olefins (NHOs) chemically transfer the base from solid phase and promote alkylation reaction on a wide range of substrates.
Chemoselective Flow Hydrogenation Approaches to Diversify the Cytotoxic Tetrahydroepoxyisoindole Carboxamide Scaffold
Publisher: Wiley
Date: 07-02-2018
C–H Functionalization Reactions of Unprotected N-Heterocycles by Gold-Catalyzed Carbene Transfer
Publisher: American Chemical Society (ACS)
Date: 07-08-2020
Convenient Access to Hydroquinone and Quinone Derivatives from Cyclobutenedione Units
Publisher: CSIRO Publishing
Date: 2010
DOI: 10.1071/CH10189
Abstract: An important synthetic method providing access to a variety of heterocyclic and polycyclic quinones and hydroquinones is described. The key transformation involves the thermal ring expansion of cyclobutenedione derivatives to quinone/hydroquinone units. The synthetic utility and recent applications of this method in natural product synthesis are also discussed.
Carbonyl–Olefin Metathesis Catalyzed by Molecular Iodine
Publisher: American Chemical Society (ACS)
Date: 14-12-2018
Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies
Publisher: American Chemical Society (ACS)
Date: 17-06-2021
Synthesis and properties of the ivyanes: the parent 1,1-oligocyclopropanes
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C0SC00500B
Hydrogen Bonding Networks Enable Brønsted Acid‐Catalyzed Carbonyl‐Olefin Metathesis**
Publisher: Wiley
Date: 10-02-2022
Abstract: Synthetic chemists have learned to mimic nature in using hydrogen bonds and other weak interactions to dictate the spatial arrangement of reaction substrates and to stabilize transition states to enable highly efficient and selective reactions. The activation of a catalyst molecule itself by hydrogen‐bonding networks, in order to enhance its catalytic activity to achieve a desired reaction outcome, is less explored in organic synthesis, despite being a commonly found phenomenon in nature. Herein, we show our investigation into this underexplored area by studying the promotion of carbonyl‐olefin metathesis reactions by hydrogen‐bonding‐assisted Brønsted acid catalysis, using hexafluoroisopropanol (HFIP) solvent in combination with para ‐toluenesulfonic acid (pTSA). Our experimental and computational mechanistic studies reveal not only an interesting role of HFIP solvent in assisting pTSA Brønsted acid catalyst, but also insightful knowledge about the current limitations of the carbonyl‐olefin metathesis reaction.
Tropylium-promoted carbonyl–olefin metathesis reactions
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8SC00907D
Abstract: The non-benzenoid aromatic tropylium ion acts as an efficient promoter for carbonyl–olefin metathesis reactions.
Activation of DMSO for Swern-type oxidation by 1,1-dichlorocycloheptatriene
Publisher: Elsevier BV
Date: 12-2014
Secondary amine catalyzed retro-aldol reactions of enals and enones: one-pot conversion of enals to α-substituted derivatives
Publisher: Elsevier BV
Date: 04-2012
Synthesis of oxime from a renewable resource for metal extraction
Publisher: Springer Science and Business Media LLC
Date: 06-03-2015
Biomimetic Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis Enabled by Hydrogen Bonding Networks
Publisher: American Chemical Society (ACS)
Date: 07-2021
DOI: 10.26434/CHEMRXIV-2021-GPLLR
Abstract: Synthetic chemists have learned to mimic nature in using hydrogen bonds and other weak interactions to dictate the spatial arrangement of reaction substrates and to stabilize transition states to enable highly efficient and selective reactions. The activation of a catalyst molecule itself by hydrogen bonding networks, in order to control its catalytic activity to achieve desired reaction outcomes is much less explored in organic synthesis, despite being a common strategy in nature. Herein, we show our investigation into this underexplored area by studying the promotion of carbonyl-olefin metathesis reactions by hydrogen bonding-assisted Brønsted acid catalysis. The carbonyl-olefin metathesis reaction has recently emerged as a powerful synthetic tool for functional group interconversion of carbonyls and alkenes. However, the application of Brønsted acid catalysts in carbonyl-olefin metathesis reaction, especially in homogeneous conditions, remains scarce and poorly understood. In this work, we report the use of hexafluoroisopropanol solvent in combination with para-toluenesulfonic acid to efficiently catalyze carbonyl-olefin metathesis reactions. Our experimental and computational mechanistic studies reveal not only an interesting role of HFIP solvent in assisting this Brønsted acid catalyzed reaction but also insightful knowledge about the current limitations of the carbonyl-olefin metathesis reaction.
Cyanomethyl anion transfer reagents for diastereoselective Corey–Chaykovsky cyclopropanation reactions
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8CC05602A
Abstract: A readily available sulfonium salt opens up new synthetic pathways to access nitrile cyclopropanes in a highly diastereoselective fashion.
Promotion of Appel-type reactions by N-heterocyclic carbenes
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9CC02132A
Abstract: N-Heterocyclic carbenes are found to mediate the Appel-type dehydrative halogenation reaction.
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View Funded ActivityDiscovery Early Career Researcher Award - Grant ID: DE150100517
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View Funded ActivityLinkage Infrastructure, Equipment And Facilities - Grant ID: LE190100160
Start Date: 2019
End Date: 12-2019
Amount: $368,994.00
Funder: Australian Research Council
View Funded Activity