Browse
Submit Data
Databases
API
Help

Dataset Information

11 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Thiocarbonyl-enabled ferrocene C-H nitrogenation by cobalt(III) catalysis: thermal and mechanochemical.

ABSTRACT: Versatile C-H amidations of synthetically useful ferrocenes were accomplished by weakly-coordinating thiocarbonyl-assisted cobalt catalysis. Thus, carboxylates enabled ferrocene C-H nitrogenations with dioxazolones, featuring ample substrate scope and robust functional group tolerance. Mechanistic studies provided strong support for a facile organometallic C-H activation manifold.

SUBMITTER: Yetra SR

PROVIDER: S-EPMC6037017 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Thiocarbonyl-enabled ferrocene C-H nitrogenation by cobalt(III) catalysis: thermal and mechanochemical.

Yetra Santhivardhana Reddy SR Shen Zhigao Z Wang Hui H Ackermann Lutz L

Beilstein journal of organic chemistry 20180625

Versatile C-H amidations of synthetically useful ferrocenes were accomplished by weakly-coordinating thiocarbonyl-assisted cobalt catalysis. Thus, carboxylates enabled ferrocene C-H nitrogenations with dioxazolones, featuring ample substrate scope and robust functional group tolerance. Mechanistic studies provided strong support for a facile organometallic C-H activation manifold. ...[more]

PMID: 30013681

Similar Datasets

Homobenzylic Oxygenation Enabled by Dual Organic Photoredox and Cobalt Catalysis.

Project description:Activation of aliphatic C(sp3)-H bonds in the presence of more activated benzylic C(sp3)-H bonds is often a nontrivial, if not impossible task. Herein we show that leveraging the reactivity of benzylic C(sp3)-H bonds to achieve reactivity at the homobenzylic position can be accomplished using dual organic photoredox/cobalt catalysis. Through a two-part catalytic system, alkyl arenes undergo dehydrogenation followed by an anti-Markovnikov Wacker-type oxidation to grant benzyl ketone products. This formal homobenzylic oxidation is accomplished with high atom economy without the use of directing groups, achieving valuable reactivity that traditionally would require multiple chemical transformations.

| S-EPMC7476681 | biostudies-literature

Mechanochemical Gold(III)-Carbon Bond Formation.

Project description:Starting from a [(MeO C^N^C)AuCl] complex as precursor, a direct substitution by C,H-activation from sp-, sp2 - or sp3 -C,H-bonds under basic conditions in a planetary ball mill was achieved. Because of the extraordinary photophysical properties of the target compounds, this protocol provides an easy access to a highly valued complex class. In contrast to existing protocols, no pre-functionalization of the starting materials is necessary and the use of expensive transition metal catalysts can be avoided, which makes this application appealing also for industrial purposes. In addition the methodology was not restricted to pincer complexes, which was demonstrated by the substitution of chelate type [(tpy)AuCl2 ] complexes.

| S-EPMC8251521 | biostudies-literature

Nanoplasmon-enabled macroscopic thermal management.

Project description:In numerous applications of energy harvesting via transformation of light into heat the focus recently shifted towards highly absorptive nanoplasmonic materials. It is currently established that noble metals-based absorptive plasmonic platforms deliver significant light-capturing capability and can be viewed as super-absorbers of optical radiation. Naturally, approaches to the direct experimental probing of macroscopic temperature increase resulting from these absorbers are welcomed. Here we derive a general quantitative method of characterizing heat-generating properties of optically absorptive layers via macroscopic thermal imaging. We further monitor macroscopic areas that are homogeneously heated by several degrees with nanostructures that occupy a mere 8% of the surface, leaving it essentially transparent and evidencing significant heat generation capability of nanoplasmon-enabled light capture. This has a direct bearing to a large number of applications where thermal management is crucial.

| S-EPMC4037716 | biostudies-literature

Cobalt Catalysis for Enantioselective Cyclobutanone Construction.

Project description:Over the past 40 years, intramolecular hydroacylation has favored five-membered rings, in preference to four membered rings. Herein, we report a catalyst derived from earth-abundant cobalt that enables preparation of cyclobutanones, with excellent regio-, diastereo-, and enantiocontrol, under mild conditions (2 mol % catalyst loading and as low as 50 °C).

| S-EPMC6824591 | biostudies-literature

Catalysis-Enabled Access to Cryptic Geldanamycin Oxides.

Project description:Catalytic, selective modifications of natural products can be a fertile platform for not only unveiling new natural product analogues with altered biological activity, but also for revealing new reactivity and selectivity hierarchies for embedded functional groups in complex environments. Motivated by these intersecting aims, we report site- and stereoselective oxidation reactions of geldanamycin facilitated by aspartyl-peptide catalysts. Through the isolation and characterization of four new geldanamycin oxides, we discovered a synergistic effect between lead peptide-based catalysts and geldanamycin, resulting in an unexpected reaction pathway. Curiously, our discoveries would likely not have been possible absent the attractive noncovalent interactions intrinsic to both the catalysts and the natural product. The result is a set of new "meta" catalytic reactions that deliver both unknown and previously incompletely characterized geldanamycin analogues. Enabled by the catalytic, site-selective epoxidation of geldanamycin, biological assays were carried out to document the bioactivities of the new compounds.

| S-EPMC7099596 | biostudies-literature

Mechanochemical Synthesis of Iron and Cobalt Magnetic Metal Nanoparticles and Iron/Calcium Oxide and Cobalt/Calcium Oxide Nanocomposites.

Project description:We report an environmentally benign and cost-effective method to produce Fe and Co magnetic metal nanoparticles as well as the Fe/Cao and Co/CaO nanocomposites by using a novel, dry mechanochemical process. Mechanochemical milling of metal oxides with a suitable reducing agent resulted in the production of magnetic metal nanoparticles. The process involved grinding and consequent reduction of low-costing oxide powders, unlike conventional processing techniques involving metal salts or metal complexes. Calcium granules were used as the reducing agent. Magnetometry measurements were performed over a large range of temperatures, from 10 to 1273?K, to evaluate the Curie temperature, blocking temperature, irreversibility temperature, saturation magnetization, and coercivity. The saturation magnetizations of the iron and cobalt nanoparticles were found to be 191 and 102?emu?g-1, respectively. The heating abilities of these nanoparticles suspended in several liquids under alternating magnetic fields were measured and the specific loss power was determined. Our results suggest that the dry mechanochemical process is a robust method to produce metallic nanoparticles and nanocomposites.

| S-EPMC6080568 | biostudies-literature

Selective electrochemical generation of benzylic radicals enabled by ferrocene-based electron-transfer mediators.

Project description:The generation and intermolecular functionalisation of carbon-centred radicals has broad potential synthetic utility. Herein, we show that benzylic radicals may be generated electrochemically from benzylboronate derivatives at low electrode potentials (ca. -0.3 V vs. Cp2Fe0/+) via single electron oxidation. Use of a catalytic quantity of a ferrocene-based electron-transfer mediator is crucial to achieve successful radical functionalisation and avoid undesirable side reactions arising from direct electrochemical oxidation or from the use of stoichiometric ferrocenium-based oxidants.

| S-EPMC5909123 | biostudies-literature

Bis(ferrocene-carboxyl-ato-?O)bis-(2-pyridyl-methanol-?N,O)cobalt(II).

Project description:The title complex mol-ecule, [Fe(2)Co(C(5)H(5))(2)(C(6)H(4)O(2))(2)(C(6)H(7)NO)(2)], has a crystallographic imposed centre of symmetry. The Co(II) atom displays a distorted octa-hedral coordination geometry, provided by the O atoms of two monodentate ferrocene-carboxyl-ate anions and by the N and O atoms of two 2-pyridyl-methanol mol-ecule. The mol-ecular conformation is stabilized by intra-molecular C-H?O hydrogen bonds.

| S-EPMC3007041 | biostudies-literature

Bis(?-ferrocene-carboxyl-ato)bis-[aqua--bis(ferrocene-carboxyl-ato)methano-l-erbium(III)] methanol disolvate.

Project description:In the centrosymmetric title coordination compound, [Er(2){Fe(C(5)H(5))(C(6)H(4)O(2))}(6)(CH(3)OH)(2)(H(2)O)(2)]·2CH(3)OH, the two Er(III) ions are bridged by two ferrocene-carboxyl-ate anions as asymmetrically bridging ligands, leading to dimeric cores. The Er(III) ion has a distorted dodeca-hedral coordination with six coordinating O atoms derived from the ferrocene-carboxyl-ate ligands and two coordinated O atoms from one water mol-ecule and one methanol mol-ecule. The asymmetric unit comprises a half of the complex mol-ecule and a methanol solvent mol-ecule. Intra-molecular O-H?O and C-H?O inter-actions occur. In the crystal, mol-ecules are linked by inter-molecular O-H?O hydrogen bonds and C-H?O as well as C-H?? inter-actions.

| S-EPMC3254279 | biostudies-other

Tris(ethyl-enediamine)-cobalt(III) diformatodioxalatoindate(III) dihydrate.

Project description:In the cation of the title compound, [Co(C(2)H(8)N(2))(3)][In(C(2)O(4))(2)(CHO(2))(2)]·2H(2)O, the Co-N bond lengths lie in the range 1.960?(5)-1.997?(5)?Å. In the anion, the In(III) atom is coordin-ated by four O atoms from two oxalato ligands and two O atoms from two formato ligands in a distorted octa-hedral geometry. Inter-molecular O-H?O and N-H?O hydrogen bonds form an extensive hydrogen-bonding network, which link the cations, anions and water mol-ecules into three-dimensional structure.

| S-EPMC3089116 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data