Oxime ≈ Oxime
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Poly(oxime–ester) Vitrimers with Catalyst-Free Bond Exchange Open
Vitrimers are network polymers that undergo associative bond exchange reactions in the condensed phase above a threshold temperature, dictated by the exchangeable bonds comprising the vitrimer. For vitrimers, chemistries reliant on poorly …
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Cross-dehydrogenative coupling for the intermolecular C–O bond formation Open
The present review summarizes primary publications on the cross-dehydrogenative C–O coupling, with special emphasis on the studies published after 2000. The starting compound, which donates a carbon atom for the formation of a new C–O bond…
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Acetone‐Linked Peptides: A Convergent Approach for Peptide Macrocyclization and Labeling Open
Macrocyclization is a broadly applied approach for overcoming the intrinsically disordered nature of linear peptides. Herein, it is shown that dichloroacetone (DCA) enhances helical secondary structures when introduced between peptide nucl…
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Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers Open
Fine-tuned organic photoredox catalysts are introduced for the metal-free alkynylation of alkylnitrile radicals generated via oxidative ring opening of cyclic alkylketone oxime ethers.
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A review on biological activities of Schiff base, hydrazone, and oxime derivatives of curcumin Open
Schiff base, hydrazone, and oxime derivatives of curcumin showed enhanced biological activities.
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Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters Open
An efficient transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters has been described. In this reaction, the B2(OH)4 reagent not only served as the boron source but also acted as an electron donor source through fo…
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Imine Hydrogels with Tunable Degradability for Tissue Engineering Open
A shortage of available organ donors has created a need for engineered tissues. In this context, polymer-based hydrogels that break down inside the body are often used as constructs for growth factors and cells. Herein, we report imine cro…
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Study of Sustainability and Scalability in the Cp*Rh(III)-Catalyzed Direct C–H Amidation with 1,4,2-Dioxazol-5-ones Open
The practical aspects of Cp*Rh(III)-catalyzed direct C–H amidation with 1,4,2-dioxazol-5-ones were investigated on the operational safety, use of green solvent, and scalability. Differential scanning calorimeter (DSC) measurement showed th…
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Metal-Free Photochemical Imino-Alkylation of Alkenes with Bifunctional Oxime Esters Open
The concurrent installation of C-C and C-N bonds across alkene frameworks represents a powerful tool to prepare motifs that are ubiquitous in pharmaceuticals and bioactive compounds. To construct such prevalent bonds, most alkene difunctio…
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Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C–H Activation Open
α,β-Unsaturated oxime pivalates are proposed to undergo reversible C(sp(2))-H insertion with cationic Rh(III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irre…
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Catalytic Alkene Difunctionalization via Imidate Radicals Open
The first catalytic strategy to harness imidate radicals has been developed. This approach enables alkene difunctionalization of allyl alcohols by photocatalytic reduction of their oxime imidates. The ensuing imidate radicals undergo conse…
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Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions Open
Cyclohexanone oxime, an important nylon-6 precursor, is conventionally synthesized through cyclohexanone-hydroxylamine (NH 2 OH) and cyclohexanone ammoxidation methodologies. These strategies require complicated procedures, high temperatur…
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Unprecedented Dinuclear CuII N,O-Donor Complex: Synthesis, Structural Characterization, Fluorescence Property, and Hirshfeld Analysis Open
An unprecedented dinuclear CuII complex, [Cu2(L2)2], derived from a salamo-like chelating ligand H2L2, was produced by the cleavage of a newly synthesized, half-salamo-like ligand HL1 (2-[O-(1-ethyloxyamide)]oxime-3,5-dichloro-phenol). Thi…
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Resurrection and Reactivation of Acetylcholinesterase and Butyrylcholinesterase Open
Organophosphorus (OP) nerve agents and pesticides present significant threats to civilian and military populations. OP compounds include the nefarious G and V chemical nerve agents, but more commonly, civilians are exposed to less toxic OP…
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Exceptionally rapid oxime and hydrazone formation promoted by catalytic amine buffers with low toxicity Open
A novel molecular strategy for accelerating hydrazone and oxime formations, using bifunctional buffer compounds that not only control pH but also catalyze the reaction, is presented.
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Synthesis of Chiral Tertiary Boronic Esters by Oxime‐Directed Catalytic Asymmetric Hydroboration Open
Chiral boronic esters are useful intermediates in asymmetric synthesis. We have previously shown that carbonyl‐directed catalytic asymmetric hydroboration (CAHB) is an efficient approach to the synthesis of functionalized primary and secon…
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<i>β</i>-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)–H bonds using a palladium catalyst Open
Palladium catalyzed selectiveβ-arylation of oxime ethers was realized using diaryliodonium salts as the key arylation reagents.
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Synthesis of α,β-Unsaturated Carbonyl-Based Compounds, Oxime and Oxime Ether Analogs as Potential Anticancer Agents for Overcoming Cancer Multidrug Resistance by Modulation of Efflux Pumps in Tumor Cells Open
Sixty-nine novel α,β-unsaturated carbonyl based compounds, including cyclohexanone, tetralone, oxime, and oxime ether analogs, were synthesized. The antiproliferative activity determined by using seven different human cancer cell lines pro…
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Photoenzymatic Synthesis of α-Tertiary Amines by Engineered Flavin-Dependent “Ene”-Reductases Open
α-Tertiary amines are a common motif in pharmaceutically important molecules but are challenging to prepare using asymmetric catalysis. Here, we demonstrate engineered flavin-dependent 'ene'-reductases (EREDs) can catalyze radical addition…
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An Enantioselective Cp<sup>x</sup>Rh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines Open
A chiral Cp x Rh III catalyst system in situ generated from a Cp x Rh I (cod) precatalyst and bis( o ‐toluoyl) peroxide as activating oxidant was developed for a C−H activation/ring‐opening sequence between aryl ketoxime ethers and 2,3‐dia…
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Iminoboronate Formation Leads to Fast and Reversible Conjugation Chemistry of α‐Nucleophiles at Neutral pH Open
Bioorthogonal reactions that are fast and reversible under physiological conditions are in high demand for biological applications. Herein, it is shown that an ortho boronic acid substituent makes aryl ketones rapidly conjugate with α‐nucl…
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Synthesis and biological evaluation of coumarin derivatives containing oxime ester as α-glucosidase inhibitors Open
In this study, potent coumarin derivatives containing oxime ester 1 ∼ 28 as α-glucosidase inhibitors were developed through a stepwise structure optimization, and the structure activity relationship was uncovered. Among them, compound 20 e…
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Preventing post-surgical cardiac adhesions with a catechol-functionalized oxime hydrogel Open
Post-surgical cardiac adhesions represent a significant problem during routine cardiothoracic procedures. This fibrous tissue can impair heart function and inhibit surgical access in reoperation procedures. Here, we propose a hydrogel barr…
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Assessment of four organophosphorus pesticides as inhibitors of human acetylcholinesterase and butyrylcholinesterase Open
Toxicity of organophosphorus compounds (OPs) remains a major public health concern due to their widespread use as pesticides and the existence of nerve agents. Their common mechanism of action involves inhibition of enzymes acetylcholinest…
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Highly Selective Radical Relay 1,4-Oxyimination of Two Electronically Differentiated Olefins Open
Radical addition reactions of olefins have emerged as an attractive tool for the rapid assembly of complex structures, and have plentiful applications in organic synthesis, however, such reactions are often limited to polymerization or 1,2…
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Scale-up of microdroplet reactions by heated ultrasonic nebulization Open
Heated ultrasonic nebulization is presented as a new way for scaling up chemical synthesis in microdroplets.
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Boronic acids facilitate rapid oxime condensations at neutral pH Open
We report here the discovery and development of boron-assisted oxime formation as a powerful connective reaction for chemical biology.
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Enantioselective Narasaka–Heck cyclizations: synthesis of tetrasubstituted nitrogen-bearing stereocenters Open
A SPINOL-derived P,N-ligand system enables Pd-catalyzed 5-exo cyclization of oxime esters with trisubstituted alkenes to generate dihydropyrroles in up to 86% yield and 95 : 5 e.r.
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FDA-Approved Oximes and Their Significance in Medicinal Chemistry Open
Despite the scientific advancements, organophosphate (OP) poisoning continues to be a major threat to humans, accounting for nearly one million poisoning cases every year leading to at least 20,000 deaths worldwide. Oximes represent the mo…
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NIR‐Sensitized Activated Photoreaction between Cyanines and Oxime Esters: Free‐Radical Photopolymerization Open
Cyanines comprising either a benzo[e]‐ or benzo[c,d]indolium core facilitate initiation of radical photopolymerization combined with high power NIR‐LED prototypes emitting at 805 nm, 860 nm, or 870 nm, while different oxime esters function…