Browse
Submit Data
Databases
API
Help

Dataset Information

17 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A Versatile Silver(I) Pentafluorooxosulfate Reagent for the Synthesis of OSF₅ Compounds.

ABSTRACT: Herein, we report the preparation of silver(I) pentafluorooxosulfate from commercially available AgF and OSF₄ . The compound is surprisingly stable in a MeCN solution. Apart from that, AgOSF₅ has been stabilised by the addition of 2,2'-bipyridine ligands. Starting from solutions of the unstabilised silver(I) salt, OSF₅ complexes with Ni^II , Cu^I , and Cu^II -centres have been obtained. In addition, AgOSF₅ has proven to be generally capable of mediating the transfer of OSF₅ groups to aryne moieties, thus furnishing a new and safe method for the preparation of OSF₅ -substituted arenes. X-ray crystal structure analysis of selected transition-metal OSF₅ compounds have revealed distorted octahedral [OSF₅ ]^- anions which are extensively stabilised by hydrogen bonding.

SUBMITTER: Haupt A

PROVIDER: S-EPMC8456853 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Modular Synthesis of a Versatile Double-Allylation Reagent for Complex Diol Synthesis.

Project description:Double-allylation reagents allow for the construction of highly complex molecules in an expedient fashion. We have developed an efficient, modular, and enantioselective approach towards accessing novel variants of these reagents through Cu/Pd-catalyzed alkenylboration of alkenylboron derivatives. Importantly, we demonstrate novel use of an allylBdan reagent directly in a stereocontrolled allylation without initial deprotection to the boronic ester. These allylation products are employed in a second intermolecular allylation to access complex diol motifs, which has yet to be shown with these types of double-allylation reagents. Overall, the modularity of this approach and the ease in which complex structural motifs can be accessed in a rapid manner signify the importance and utility of this method.

| S-EPMC8893119 | biostudies-literature

A versatile snap chip for high-density sub-nanoliter chip-to-chip reagent transfer.

Project description:The coordinated delivery of minute amounts of different reagents is important for microfluidics and microarrays, but is dependent on advanced equipment such as microarrayers. Previously, we developed the snap chip for the direct transfer of reagents, thus realizing fluidic operations by only manipulating microscope slides. However, owing to the misalignment between arrays spotted on different slides, millimeter spacing was needed between spots and the array density was limited. In this work, we have developed a novel double transfer method and have transferred 625 spots cm(-2), corresponding to >10000 spots for a standard microscope slide. A user-friendly snapping system was manufactured to make liquid handling straightforward. Misalignment, which for direct transfer ranged from 150-250 ?m, was reduced to <40 ?m for double transfer. The snap chip was used to quantify 50 proteins in 16 samples simultaneously, yielding limits of detection in the pg/mL range for 35 proteins. The versatility of the snap chip is illustrated with a 4-plex homogenous enzyme inhibition assay analyzing 128 conditions with precise timing. The versatility and high density of the snap chip with double transfer allows for the development of high throughput reagent transfer protocols compatible with a variety of applications.

| S-EPMC4493572 | biostudies-literature

Serinol-Based Versatile Disulfide-Reducing Reagent.

Project description:Here, we report the synthesis of disulfide-reducing agents 2-(dibenzylamino) propane-1,3-dithiol (DPDT) and 2-(dibenzylamino)-2-methylpropane-1,3-dithiol (DMPDT) from serinol and methyl serinol, respectively. DPDT was found to show greater stability than DMPDT. Hence, the effectiveness of DPDT as a reducing agent was evaluated in both liquid and solid phases. The reducing capacity of this agent was comparable to that of DTT.

| S-EPMC10384529 | biostudies-literature

Synthesis and shift-reagent-assisted full NMR assignment of bacterial (Z8,E2,ω)-undecaprenol.

Project description:The repeating isoprene unit is a fundamental biosynthetic motif. The repetitive structure presents challenges both for synthesis and for structural characterization. In this synthesis of the (Z8,E2,ω)-undecaprenol of prokaryotic glycobiology, we exemplify solutions to these challenges. Allylation of sulfone-derived carbanions controlled the stereochemistry, and its proof-of-structure was secured by Eu(hfc)3 complexation to disperse the overlaid resonances of its 1H NMR spectrum.

| S-EPMC5749266 | biostudies-literature

Versatile dehydrogenation of carbonyls enabled by an iodine(III) reagent.

Project description:We report the utilisation of an iodine(III) reagent to access α,β-unsaturated carbonyls from the corresponding silyl enol ethers of ketones and aldehydes, and from enol phosphates of lactones and lactams. The transformation is rapid, scalable, and can be carried out in one pot, directly dehydrogenating saturated carbonyls.

| S-EPMC11310745 | biostudies-literature

Designer HF-based fluorination reagent: highly regioselective synthesis of fluoroalkenes and gem-difluoromethylene compounds from alkynes.

Project description:Hydrogen fluoride (HF) and selected nonbasic and weakly coordinating (toward cationic metal) hydrogen-bond acceptors (e.g., DMPU) can form stable complexes through hydrogen bonding. The DMPU/HF complex is a new nucleophilic fluorination reagent that has high acidity and is compatible with cationic metal catalysts. The gold-catalyzed mono- and dihydrofluorination of alkynes using the DMPU/HF complex yields synthetically important fluoroalkenes and gem-difluoromethlylene compounds regioselectively.

| S-EPMC4210154 | biostudies-literature

Direct electrophilic and radical isoperfluoropropylation with i-C3F7-Iodine(III) reagent (PFPI reagent).

Project description:The isoperfluoropropyl group (i-C3F7) is an emerging motif in pharmaceuticals, agrichemicals and functional materials. However, isoperfluoropropylated compounds remain largely underexplored, presumably due to the lack of efficient access to these compounds. Herein, we disclose the practical and efficient isoperfluoropropylation of aromatic C-H bonds through the invention of a hypervalent-iodine-based reagent-PFPI reagent, that proceeds via a Ag-X coupling process. The activation of the PFPI reagent without any catalysts or additives was demonstrated in the synthesis of isoperfluoropropylated electron-rich heterocycles, while its activity under photoredox catalysis was shown in the synthesis of isoperfluoropropylated non-activated arenes. Detailed mechanistic experiments and DFT calculations revealed a SET-induced concerted mechanistic pathway in the photoredox reactions. In addition, the unique conformation of i-C3F7 in products, that involved intramolecular hydrogen bond was investigated by X-ray single-crystal diffraction and variable-temperature NMR experiments.

| S-EPMC10449889 | biostudies-literature

High-load, oligomeric dichlorotriazine: a versatile ROMP-derived reagent and scavenger.

Project description:A new high-load, soluble oligomeric dichlorotriazine (ODCT) reagent derived from ring-opening metathesis polymerization (ROMP) is reported as an effective coupling reagent, scavenger of nucleophilic species, and activator of DMSO for the classic Swern oxidations. Two variants of this reagent (2G)ODCT 4 and (1G)ODCT 16, possessing theoretical loads of 5.3 and 7.3 mmol/g, respectively, have been synthesized. Preparation was accomplished via simple synthetic protocols affording free flowing powders, amenable for large-scale production. Removal of the spent oligomeric reagent was achieved via either precipitation of the spent reagent or simple filtration utilizing a silica SPE, followed by solvent removal, to deliver products in excellent yield and purity. In addition, the corresponding norbornenyl monomer 3 was successfully demonstrated in a couple-ROMP-filter protocol utilizing in situ polymerization, achieving comparable results versus the corresponding oligomeric variant.

| S-EPMC3271944 | biostudies-literature

2-Diazo-1-(4-hydroxyphenyl)ethanone: a versatile photochemical and synthetic reagent.

Project description:?-Diazo arylketones are well-known substrates for Wolff rearrangement to phenylacetic acids through a ketene intermediate by either thermal or photochemical activation. Likewise, ?-substituted p-hydroxyphenacyl (pHP) esters are substrates for photo-Favorskii rearrangements to phenylacetic acids by a different pathway that purportedly involves a cyclopropanone intermediate. In this paper, we show that the photolysis of a series of ?-diazo-p-hydroxyacetophenones and p-hydroxyphenacyl (pHP) ?-esters both generate the identical rearranged phenylacetates as major products. Since ?-diazo-p-hydroxyacetophenone (1a, pHP N2) contains all the necessary functionalities for either Wolff or Favorskii rearrangement, we were prompted to probe this intriguing mechanistic dichotomy under conditions favorable to the photo-Favorskii rearrangement, i.e., photolysis in hydroxylic media. An investigation of the mechanism for conversion of 1a to p-hydroxyphenyl acetic acid (4a) using time-resolved infrared (TRIR) spectroscopy clearly demonstrates the formation of a ketene intermediate that is subsequently trapped by solvent or nucleophiles. The photoreaction of 1a is quenched by oxygen and sensitized by triplet sensitizers and the quantum yields for 1a-c range from 0.19 to a robust 0.25. The lifetime of the triplet, determined by Stern-Volmer quenching, is 31 ns with a rate for appearance of 4a of k = 7.1 × 10(6) s(-1) in aq. acetonitrile (1?:?1 v?:?v). These studies establish that the primary rearrangement pathway for 1a involves ketene formation in accordance with the photo-Wolff rearrangement. Furthermore we have also demonstrated the synthetic utility of 1a as an esterification and etherification reagent with a variety of substituted ?-diazo-p-hydroxyacetophenones, using them as synthons for efficiently coupling it to acids and phenols to produce pHP protect substrates.

| S-EPMC3939782 | biostudies-literature

Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene.

Project description:The use of vinyl electrophiles in synthesis has been hampered by the lack of access to a suitable reagent that is practical and of appropriate reactivity. In this work we introduce a vinyl thianthrenium salt as an effective vinylating reagent. The bench-stable, crystalline reagent can be readily prepared from ethylene gas at atmospheric pressure in one step and is broadly useful in the annulation chemistry of (hetero)cycles, N-vinylation of heterocyclic compounds, and palladium-catalyzed cross-coupling reactions. The structural features of the thianthrene core enable a distinct synthesis and reactivity profile, unprecedented for other vinyl sulfonium derivatives.

| S-EPMC8391941 | biostudies-literature