Philip Wai Hong Chan

Rhodium(i)-catalysed cycloisomerisation/6π electrocyclisation of 5-(ethynylamino)pent-2-yn-1-yl esters to 2,3-dihydrobenzo[f]indoles

Publisher: Royal Society of Chemistry (RSC)

Date: 2022

DOI: 10.1039/D2NJ01992B

Abstract: A rare instance in rhodium catalysis of an in situ formed rhodacycle that undergoes a formal 1,8-acyloxy migration-initiated reductive elimination.

THF-enabled PtBr₂-catalyzed desymmetric hydrogenative [3 + 2] cycloaddition of 2-alkynylbenzaldehyde-tethered cyclohexadienones

Publisher: Royal Society of Chemistry (RSC)

Date: 2022

DOI: 10.1039/D2QO00593J

Abstract: A rare instance in platinum catalysis of an in situ formed Pt-bound benzopyrylium species that undergoes [3 + 2] cycloaddition with an electron-deficient alkene tether followed by THF-enabled hydrogenation.

Copper(I)-catalysed site-selective C(sp ³)–H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T

Publisher: Springer Science and Business Media LLC

Date: 07-2021

DOI: 10.1038/S41467-021-23988-Y

Abstract: Strategies that enable intermolecular site-selective C–H bond functionalisation of organic molecules provide one of the cornerstones of modern chemical synthesis. In chloroalkane synthesis, such methods for intermolecular site-selective aliphatic C–H bond chlorination have, however, remained conspicuously rare. Here, we present a copper(I)-catalysed synthetic method for the efficient site-selective C( sp 3 )–H bond chlorination of ketones, ( E )-enones and alkylbenzenes by dichloramine-T at room temperature. A key feature of the broad substrate scope is tolerance to unsaturation, which would normally pose an immense challenge in chemoselective aliphatic C–H bond functionalisation. By unlocking dichloramine-T’s potential as a chlorine radical atom source, the product site-selectivities achieved are among the most selective in alkane functionalisation and should find widespread utility in chemical synthesis. This is exemplified by the late-stage site-selective modification of a number of natural products and bioactive compounds, and gram-scale preparation and formal synthesis of two drug molecules.

Chiral Gold Complex Catalyzed Cycloisomerization/Regio- and Enantioselective Nitroso-Diels–Alder Reaction of 1,6-Diyne Esters with Nitrosobenzenes

Publisher: American Chemical Society (ACS)

Date: 03-06-2022

DOI: 10.1021/ACSCATAL.2C01680

Gold Catalysed 1,4-Enyne Acetate Strategy for the Synthesis of 1H-Indenes and Partially Hydrogenated Methanonaphtho[1,2-c]furan-1,3(4H)-diones

Publisher: CSIRO Publishing

Date: 2020

DOI: 10.1071/CH20175

Abstract: A synthetic method to prepare 1H-indenes and partially hydrogenated methanonaphtho[1,2-c]furan-1,3(4H)-diones from gold(i)-catalysed 1,4-enyne acetate cycloisomerisation and oxidation or Diels–Alder reaction with maleic anhydride is described. The proposed mechanism involves Rautenstrauch rearrangement of the 1,4-enyne motif to give an insitu formed 1,3-cyclopentadiene intermediate. This is followed by 6-endo-dig cyclisation of the cyclic adduct and oxidation to give the aromatic carbocycle or Diels–Alder reaction with maleic anhydride to afford the bridged furan product.

Gold and Brønsted Acid Catalyzed Spirocyclization of 2- and 3-Indolyl-Tethered 1,4-Enyne Acetates to Spiro[4,n]alkyl[b]indoles

Publisher: American Chemical Society (ACS)

Date: 26-03-2020

DOI: 10.1021/ACS.ORGLETT.0C00929

Recent Advances in the Gold-Catalyzed Reactions of Propargyl Esters

Publisher: American Chemical Society (ACS)

Date: 06-06-2023

DOI: 10.1021/ACS.ACCOUNTS.3C00057

Coassembled Nitric Oxide-Releasing Nanoparticles with Potent Antimicrobial Efficacy against Methicillin-Resistant Staphylococcus aureus (MRSA) Strains

Publisher: American Chemical Society (ACS)

Date: 11-08-2022

DOI: 10.1021/ACSAMI.2C08833

Abstract: Nitric oxide (NO)-releasing nanoparticles are effective nanomedicines with erse therapeutic advantages compared with small molecule-based NO donors. Here, we report a new class of furoxan-based NO-releasing nanoparticles using a simple, creative yet facile coassembly approach. This is the first time we demonstrated that the coassembled NO-releasing nanoparticles with poly(ethylene glycol)

Copper catalyzedN-formylation of α-silyl-substituted tertiaryN-alkylamines by air

Publisher: Royal Society of Chemistry (RSC)

Date: 2020

DOI: 10.1039/D0GC01242D

Abstract: A site-selective synthetic method to prepare N -formyl amines efficiently from copper( i )-catalyzed oxidation of α-silylamines by air at room temperature is presented.

A robust photoluminescence screening assay identifies uracil-DNA glycosylase inhibitors against prostate cancer

Publisher: Royal Society of Chemistry (RSC)

Date: 2020

DOI: 10.1039/C9SC05623H

Abstract: The discovery of UDG inhibitors against prostate cancer by using a robust photoluminescence screening assay that can avoid false negatives arising from the background fluorescence.

Gold-Catalyzed Formal [4 + 2] Cycloaddition of 5-(Ethynylamino)pent-2-yn-1-yl Esters to 1,2,3,5-Tetrahydrobenzo[g]quinolines

Publisher: American Chemical Society (ACS)

Date: 26-02-2018

DOI: 10.1021/ACS.ORGLETT.8B00267

Abstract: A synthetic method to prepare 1,2,3,5-tetrahydrobenzo[ g]quinolines efficiently that relies on gold(I)-catalyzed cycloisomerization of 5-(ethynylamino)pent-2-yn-1-yl esters at room temperature under atmospheric conditions is described. The proposed reaction mechanism presents a unique instance of an in situ formed allenic ester and gold keteniminium species to undergo a formal [4 + 2] cycloaddition pathway.

Gold catalysed site-selective cross-coupling of tertiary α-silylamines with 1-iodoalkynes under UVA LED light

Publisher: Royal Society of Chemistry (RSC)

Date: 2023

DOI: 10.1039/D2QO01581A

Abstract: A synthetic method that relies on a gold( i , i ) complex and UVA LED light source to catalyse the α-alkynylation of tertiary α-silylamines by 1-iodoalkynes is described.

Minisci‐Type Alkylation of N‐Heteroarenes by N‐(Acyloxy)phthalimide Esters Mediated by a Hantzsch Ester And Blue LED Light

Publisher: Wiley

Date: 05-01-2022

DOI: 10.1002/ADSC.202101195

Abstract: A synthetic method that enables the Hantzsch ester‐mediated Minisci‐type C2‐alkylation of quinolines, isoquinolines and pyridines by N ‐(acyloxy)phthalimide esters (NHPI) under blue LED (light emitting diode) light (456 nm) is described. Achieved under mild reaction conditions at room temperature, the metal‐free synthetic protocol was shown to be applicable to primary, secondary and tertiary NHPIs to give the alkylated N ‐heterocyclic products in yields of 21–99%. On introducing a chiral phosphoric acid, an asymmetric version of the reaction was also realised and provided product enantiomeric excess (ee) values of 53–99%. The reaction mechanism was delineated to involve excitation of an electron‐donor acceptor (EDA) complex, formed from weak electrostatic interactions between the Hantzsch ester and NHPI, which generates the posited radical species of the redox active ester that undergoes addition to the N ‐heterocycle. magnified image

UVA LED Light Promoted Cross‐Coupling of Tertiary α‐Silylamines with 1‐Iodoalkynes

Publisher: Wiley

Date: 20-06-2023

DOI: 10.1002/AJOC.202300221

Abstract: A synthetic strategy that exploits the formation of an electron donor‐acceptor (EDA) complex between a tertiary α‐ silylamine and 1‐iodoalkyne under UVA LED (light emitting diode) light ( λ max =365 nm) to prepare propargyl amines is described. The site‐ and chemoselective synthetic method was shown to tolerate a wide range of functional groups to give the α ‐alkynylation product in good to excellent yields. The usefulness of the C(sp)–C(sp 3 ) bond formation protocol was also exemplified by the late‐stage functionalisation of a variety of natural products and bioactive compounds.

Organocatalytic α‐Aminoalkylation of Azomethine Imines by α‐Silylamines under Blue LED Light

Publisher: Wiley

Date: 10-07-2023

DOI: 10.1002/ADSC.202300463

Abstract: A synthetic method to prepare 1,2‐diamines efficiently that relies on the 4CzPN‐catalysed α ‐aminoalkylation of azomethine imines by secondary and tertiary α ‐silylamines under blue light emitting diode (LED) light (456 nm) is described. Achieved under metal‐ and additive‐free reaction conditions at room temperature, the synthetic protocol was shown to afford product yields up to 99% and applicable to the late‐stage functionalisation of three drug molecules and the gramme‐scale preparation of one ex le.

Key Enabling Technologies for Drones

Publisher: IEEE

Date: 08-2020

DOI: 10.1109/DSD51259.2020.00083

Organocatalytic alkylation and photoorganocatalyst-free acylation of azomethine imines by Hantzsch esters under blue LED light

Publisher: Royal Society of Chemistry (RSC)

Date: 2023

DOI: 10.1039/D3NJ03780K

Chiral Brønsted Acid Catalyzed Enantioselective Dehydrative Nazarov-Type Electrocyclization of Aryl and 2-Thienyl Vinyl Alcohols

Publisher: American Chemical Society (ACS)

Date: 09-04-2018

DOI: 10.1021/JACS.8B02339

Abstract: An efficient chiral Brønsted acid-catalyzed enantioselective dehydrative Nazarov-type electrocyclization (DNE) of electron-rich aryl- and 2-thienyl-β-amino-2-en-1-ols is described. The 4π conrotatory electrocyclization reaction affords access to a wide variety of the corresponding 1 H-indenes and 4 H-cyclopenta[ b]thiophenes in excellent yields of up to 99% and enantiomeric excess (ee) values of up to 99%. Experimental and computational studies based on a proposed intimate contact ion-pair species that is further assisted by hydrogen bonding between the amino group of the substrate cation and chiral catalyst anion provide insight into the observed product enantioselectivities.

Silver-Catalyzed 1,3-Acyloxy Migration/Diels–Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines

Publisher: American Chemical Society (ACS)

Date: 07-03-2017

DOI: 10.1021/ACS.JOC.7B00048

Abstract: A synthetic method to prepare partially hydrogenated isoquinolines efficiently from silver-mediated [3,3]-sigmatropic rearrangement/Diels-Alder reaction of 1,9-dien-4-yne esters is described. The reactions were shown to be robust with a wide variety of substitution patterns tolerated to provide the corresponding nitrogen-containing heterocyclic products in good to excellent yields. This includes ex les containing a bridgehead sp

Gold-Catalyzed Double Cycloisomerization of 1-Ene-4,10-diynyl Esters to Bicyclo[6.3.0]undeca-2,4,9-trienyl Esters

Publisher: Wiley

Date: 10-10-2018

DOI: 10.1002/ANIE.201809376

Abstract: A synthetic method to prepare bicyclo[6.3.0]undeca-2,4,9,trienyl esters efficiently from gold(I)-catalyzed Rautenstrauch rearrangement/1,5-hydride shift/8-endo-dig cyclization of 1-ene-4,10-diynyl esters is described. The suggested double cycloisomerization mechanism delineates the first ex le of an unactivated all-carbon tethered 1,7-enyne, either preformed or formed in situ, which undergoes an 8-endo-dig cyclization pathway to give a cyclooctane motif. It also offers an extremely rare synthetic method in organic chemistry that can sequentially assemble both ring components of the bicyclic motif from an acyclic precursor in one step.

University Of Zurich

Location: Switzerland

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Eindhoven University Of Technology

Location: Netherlands

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IMEC

Location: Netherlands

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University Of Bristol School Of Chemistry

Location: United Kingdom of Great Britain and Northern Ireland

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University Of Oxford

Location: United Kingdom of Great Britain and Northern Ireland

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Discovery Projects - Grant ID: DP160101682

Start Date: 2016

End Date: 12-2019

Amount: $499,671.00

Funder: Australian Research Council

Discovery Projects - Grant ID: DP210103425

Start Date: 01-2021

End Date: 01-2025

Amount: $230,000.00

Funder: Australian Research Council

Industrial Transformation Training Centres - Grant ID: IC190100034

Start Date: 12-2020

End Date: 12-2025

Amount: $3,574,272.00

Funder: Australian Research Council

Industrial Transformation Training Centres - Grant ID: IC230100046

Start Date: 2023

End Date: 12-2027

Amount: $5,000,000.00

Funder: Australian Research Council