A5071016211- Sulfur-Based Synthesis Techniques
- Catalytic Cross-Coupling Reactions
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Nanocluster Synthesis and Applications
- Fullerene Chemistry and Applications
- Radical Photochemical Reactions
- Catalytic C–H Functionalization Methods
- Synthesis of Indole Derivatives
- Chemical Synthesis and Reactions
- Organometallic Complex Synthesis and Catalysis
- Fluorine in Organic Chemistry
- Boron and Carbon Nanomaterials Research
- Asymmetric Hydrogenation and Catalysis
- Nanomaterials for catalytic reactions
- Carbon Nanotubes in Composites
- Pharmacological Effects and Toxicity Studies
- Graphene research and applications
- Organoboron and organosilicon chemistry
- Advanced Nanomaterials in Catalysis
- Multicomponent Synthesis of Heterocycles
- Oxidative Organic Chemistry Reactions
- Chemical Reactions and Mechanisms
- Nanoplatforms for cancer theranostics
- Synthesis and Catalytic Reactions
Nagoya University
2016-2025
Queen's University
2023
Sichuan University
2022
Carl von Ossietzky Universität Oldenburg
2022
Gurukul Kangri Vishwavidyalaya
2022
Universidade Estadual Paulista (Unesp)
2022
Korea Advanced Institute of Science and Technology
2018
Japan Science and Technology Agency
2007-2008
Sulfones are common, readily available reagents that have recently attracted attention as versatile for cross-coupling reactions. This Review summarizes advances in desulfonylative transformations of sulfones affected by molecular catalysis, including transition-metal catalysts, photocatalysts, and organocatalysts. In addition to catalyst choice, the design sulfonyl group is a critical factor control reactivity. The concepts presented herein will provide new strategies construct diverse...
This perspective highlights advances in the preparation and understanding of metal nanoclusters stabilized by organic ligands with a focus on N-heterocyclic carbenes (NHCs). We demonstrate need for clear relationship between NHC properties their resulting nanocluster structure properties. emphasize importance balancing stability introduction reactive sites catalytic applications better how these clusters interact environments effective use biological applications. The impact atom-scale...
Triarylmethanes and related compounds are fascinating molecules because of their structural physical properties, many potential applications in organic functional materials, high biological activity. Recently, catalysis has provided new synthesis routes to triarylmethanes with selectivity diversity, including the possibility preparing enantiomerically enriched derivatives, which is typically challenging using classical methods. This Perspective reviews recent advances approaches well-defined...
Highly stable gold nanoparticles (Au NPs) functionalized by bidentate N-heterocyclic carbene (NHC) ligands have been synthesized top-down and bottom-up approaches. A detailed study of the effect alkylation, denticity, method synthesis has led to production NHC-stabilized with higher thermal stability than bi- tridentate thiol-protected Au NPs monodentate NPs. Importantly, NHC-protected also displayed unprecedented external thiol, which an unsolved problem date all nanoparticles. Thus,...
We describe the development of a nickel-catalyzed Suzuki–Miyaura cross-coupling tertiary benzylic and allylic sulfones with arylboroxines. A variety sulfones, which can easily be prepared via deprotonation–alkylation route, were reacted to afford symmetric unsymmetric quaternary products in good yields. highlight use either BrettPhos or Doyle's phosphines as effective ligands for these challenging desulfonative coupling reactions. The utility this methodology was demonstrated concise...
Abstract NHC‐Au I complexes were used to prepare stable, water‐soluble, NHC‐protected gold nanoparticles. The charged nature of the nanoparticles permitted analysis by polyacrylamide gel electrophoresis (PAGE), which showed that highly monodisperse, with tunable core diameters between 2.0 and 3.3 nm depending on synthesis conditions. Temporal, thermal, chemical stability determined be high. Treatment thiols caused etching particles after 24 h; however larger plasmonic greater resistance...
Abstract Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive readily available template. The three aryl groups were installed through two sequential palladium‐catalyzed CH arylation reactions, followed by arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using haloarenes boronic acids, is also for the preparation of...
Abstract The Suzuki–Miyaura cross-coupling is one of the most often utilized reactions in synthesis pharmaceutical compounds and conjugated materials. In its common form, reaction joins two sp 2 -functionalized carbon atoms to make a biaryl or diene/polyene unit. These substructures are widely found natural products small molecules thus has been proposed as key for automated assembly such molecules, using protecting group chemistry affect iterative coupling. We present herein, significant...
The development of fluorinated sulfone derivatives as versatile electrophiles for Suzuki–Miyaura cross-coupling reactions is described. Introducing electron-withdrawing groups on the aryl ring facilitates Pd-catalyzed activation C–SO2 bonds. Cross-coupling with are reported, leading to a variety multiply arylated products in good yields. reactivity this unusual electrophile benchmarked versus common and its use iterative cross-couplings concise synthesis biologically active molecules
A series of chiral Au 13 nanoclusters were synthesized via the direct reduction achiral dinuclear Au( i ) halide complexes ligated by ortho -xylyl-linked bis- N -heterocyclic carbene (NHC) ligands.
Herein we report the first chiral Au10 nanoclusters stabilized by bis N-heterocyclic carbene (bisNHC) ligands. ESI-MS and single-crystal X-ray crystallography confirmed molecular formula to be [Au10(bisNHC)4Br2](O2CCF3)2. The nanocluster adopts a linear edge-shared tetrahedral geometry with prolate shape. DFT calculations provide insight into electronic structure, optical absorption, circular dichroism (CD) characteristics of this unique nanocluster. CD spectra demonstrate chirality transfer...
A series of chiral Au13 nanoclusters were synthesized via the direct reduction dinuclear Au(I) halide complexes ligated by dioxalone-linked bis-N-heterocyclic carbene (bisNHC) ligands. Electrospray ionization mass spectrometry, nuclear magnetic resonance spectroscopy, and density functional theory (DFT) calculations confirmed molecular formula to be [Au13(bisNHC)4I4]+, with a arrangement four ditopic NHC ligands around icosahedral core. Circular dichroism (CD) spectroscopy two enantiomers...
A new organoboron-based arylation and alkenylation of C60 catalyzed by a rhodium complex was developed. treatment with an organoboron compound in the presence catalytic amount [Rh(cod)(CH3CN)2]BF4 H2O/1,2-Cl2C6H4 furnished functionalized fullerene (R−C60−H) good to excellent selectivity. Aryl, heteroaryl, alkenyl groups can be installed reactions using corresponding boronic acids, pinacol esters, potassium trifluoroborates.
An aziridine moiety on the fullerene core can serve as an acid-triggered reacting template for controlled synthesis of a range functionalized fullerenes that are otherwise difficult to synthesize in efficient and selective manner. A copper-catalyzed aziridination C60 practical aziridinofullerene 1 acid-catalyzed reactions with mono- bifunctional nucleophiles well alkynes described. The rapid generation structural diversity single chemical operation using common platform is notable.
The selective synthesis of multiarylated acetonitriles via sequential palladium-catalyzed arylations chloroacetonitrile is reported. three aryl groups are installed a Pd-catalyzed Suzuki–Miyaura cross coupling reaction followed by back-to-back C–H to afford triarylacetonitriles in steps with no over-arylation at any step. triarylacetonitrile products can be converted into highly functionalized species including tetraarylmethanes. This new strategy provides rapid access variety unsymmetrical...
A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. variety both sulfone arene substrates were reacted to afford symmetric nonsymmetric triarylmethanes in good yields. Further transformations the resulting application concise synthesis a bactericidal agent analogue also demonstrated.
Herein, we describe the synthesis of a toroidal Au
The desulfonylative radical addition of tertiary alkyl groups to gem-difluoroalkenes by photoredox Ir-catalyst is described. This method exhibits broad substrate scope, affording structurally diverse (E)-fluoroalkene derivatives in a highly stereoselective manner. resulting (E)-fluoroalkenes were converted into complex fused cyclic compounds intramolecular cyclization reactions. Control experiments and theoretical calculations are consistent with single Ir catalyst playing the dual role...
A Pd-catalyzed tetraallylation of C60 that selectively occurs with an unsymmetrical addition pattern has been established. Treatment CH2═CHCH2Cl, CH2═CHCH2SnBu3, and PdCl2[P(OPh)3]2 in 1,2-Cl2C6H4 at 50 °C afforded the tetraallylated fullerene 74% yield virtually complete regioselectivity. Mechanistic investigations showed (i) proceeds through consecutive nucleophilic/electrophilic allylations [likely via a bis(π-allyl)palladium intermediate] (ii) both steric (for first diallylation)...
The Pd-catalyzed desulfonative cross-coupling reaction of benzylic sulfone derivatives with 1,3-oxazoles via a deprotonative pathway has been developed. Broad substrate scope for both and 1,3-oxazole partners is observed, affording variety 1,3-oxazole-containing triarylmethanes. Sulfone that are primary benzylic, secondary benzhydryl all effective. Using this method, the straightforward synthesis multiply arylated structures demonstrated.
Abstract α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting improved biological activity stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes still rare. Herein we describe Pd-catalyzed Suzuki-Miyaura cross-coupling benzylic triflones arylboronic acids affording structurally diverse diarylmethanes. The ease synthesis fluorinated as key starting materials enables powerful...
The unprecedented synthesis of gem-difluoroalkenes through the Ramberg–Bäcklund reaction alkyl triflones is described herein. Structurally diverse, fully substituted that are difficult to prepare by other methods can be easily prepared from readily available treatment with specific Grignard reagents. Experimental and computational studies provide insight into unique critical role reagent, which serves both as a base remove α-proton Lewis acid assist C–F bond activation.
A new method for the generation of tertiary radicals through single electron reduction alkylsulfones promoted by Zn and 1,10-phenanthroline has been developed.
N-heterocyclic carbene (NHC)-protected gold nanoclusters display high stability and photoluminescence, making them well-suited for fluorescence imaging photodynamic therapeutic applications. We report herein the synthesis of two bisNHC-protected Au13 with π-extended aromatic systems. Depending on position system, changes to structure ligand shell in cluster are observed, ability correlate increases rigidity quantum yield. Density functional theory analysis reveals that both synthesized...