Structure and Reactivity of N-Heterocyclic Alkynyl Hypervalent Iodine Reagents

Structure and Reactivity of N-Heterocyclic Alkynyl Hypervalent Iodine Reagents
Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents have grow to be in style reagents for the alkynylation of radicals and nucleophiles, however solely supply restricted potentialities for additional construction and reactivity fine-tuning. Herein, we report the synthesis of recent N -heterocyclic hypervalent iodine reagents with elevated structural flexibility based mostly on amide, amidine and sulfoximine scaffolds.
Strong state constructions of the reagents are reported and the evaluation of the I-C alkyne bond lengths allowed assessing the trans -effect of the completely different substituents. Molecular electrostatic potential (MEP) maps of the reagents, derived from DFT computations, revealed much less pronounced σ-hole areas for sulfonamide-based compounds.
Most reagents reacted nicely within the alkynylation of β-ketoesters. The alkynylation of thiols afforded extra variable yields, with compounds with a stronger σ-hole reacting higher. In metal-mediated transformations, the N -heterocyclic hypervalent iodine reagents gave inferior outcomes when in comparison with the O -based EBX reagents.

Bis(trifluoromethyl)amido Complexes of Copper and Silver: Steady and storable N(CF3)2 switch reagents

Fluorinated teams are important for drug design, agro-che-micals, and supplies science. The bis(trifluoro-methyl)–amino group is an instance for a steady group that has a excessive potential. Whereas the variety of molecules containing per-fluoro-alkyl, perfluoro-alkoxy, and different fluorinated teams is steadily growing, exampl-es with the N(CF3)2 group are uncommon.
One cause is that switch reagents are scarce and metal-based storable reagents are unknown. Right here, we current a set of CuI and AgI bis(trifluoromethyl)amido complexes stabilized by N- and P-donor ligands with un-pre-ce–dented stability. The complexes are steady solids that may even be manipulated in air for a short while. They’re bis(trifluoro-methyl)amination reagents as proven by nucleo-philic substitution and Sandmeyer reactions.
Along with a sequence of benzylbis(trifluoromethyl)amines, 2-bis(trifluoro-methyl)–amino acetate was obtained that upon hydrolysis offers the fluorinated amino acid N,N-bis(trifluoromethyl)glycine.

Diastereoselective Additions of Allylmagnesium Reagents to α-Substituted Ketones When Stereochemical Fashions Can not Be Used

The stereoselectivities of reactions of allylmagnesium reagents with chiral ketones can’t be simply defined by stereochemical fashions. Competitors experiments point out that the complexation step shouldn’t be reversible, so nucleophiles can’t entry the widest vary of doable encounter complexes and due to this fact can’t be analyzed simply utilizing obtainable fashions.
Structure and Reactivity of N-Heterocyclic Alkynyl Hypervalent Iodine Reagents
However, additions of allylmagnesium reagents to a ketone can nonetheless be stereoselective offered that the carbonyl group adopts a conformation that results in one face being fully blocked from the strategy of the allylmagnesium reagent.

Improvement of a triazinedione-based dehydrative condensing reagent containing 4-(dimethylamino)pyridine as an acyl switch catalyst

A brand new triazinedione-based reagent, (N,N’-dialkyl)triazinedione-4-(dimethylamino)pyridine (ATD-DMAP) was developed for the operationally easy dehydrative condensation of carboxylic acids. This reagent includes an ATD core and DMAP because the leaving group, which is liberated into the response system to speed up acyl switch reactions.
Upon including ATD-DMAP to a mix of carboxylic acids and alcohols within the presence of an amine base, the corresponding esters have been shaped quickly at room temperature. Furthermore, dehydrative condensation between carboxylic acids and amines utilizing ATD-DMAP proceeded in excessive yield.

N-Acyltriazinedione; a Novel Acylating Reagent Synthesized from a Triazinone-Kind Condensing Reagent

On this paper, we report the synthesis of N-acyltriazinedione through the sudden O-N acyl rearrangement of acyloxytriazinone and its utility as an acylating reagent. N-Acyltriazinedione might be remoted by silica gel column chromatography and reacts with amines within the absence of any base to provide the corresponding amides in good yields.

Tuning a pyrazoline-based fluorogenic reagent, 3-naphthyl-1-(4-trifluoromethyl)-5-(4-carboxy phenyl)-2-pyrazoline for delicate precolumn derivatization of aliphatic alcohols and hint evaluation by RP-HPLC with fluorescence detection

A brand new member of the pyrazoline household, 3-naphthyl-1-(4-trifluoromethyl)-5-(4-carboxy phenyl)-2-pyrazoline has been evaluated as a precolumn derivatization reagent for the evaluation of major alcohols utilizing HPLC. The simultaneous separation of eight alcohol derivatives (C1 -C8 ) inside 15 min was achieved on a reverse-phase C8 column with an isocratic elution mode.
The derivatives have been detected with fluorescence at an emission wavelength of 470 nm when excited at 360 nm. The identification of the corresponding derivatives was carried out by LC-MS/MS and all confirmed their attribute mum or dad peak in destructive ion mode. The proposed methodology was validated utilizing regular analytical instruments and was discovered to be glorious. As a preliminary utility, our methodology was used to find out ethanol focus in alcohol-containing sweets and cough syrup.

Comparative assessments of the biodistribution and toxicity of oxidized single-walled carbon nanotubes dispersed with two completely different reagents after intravenous injection

The current examine in contrast the consequences of two commonly-used dispersants, bovine serum albumin (BSA) and polyethylene glycol (PEG), on the biodistribution and toxicity of oxidized super-growth single-wall carbon nanotubes (oxSG) injected intravenously into mice over Three months. About 1-2% of the injected dose (ID) of oxSG dispersed in BSA (oxSG-BSA) was current within the lungs in any respect time factors.
Against this, about 15% of the ID of oxSG dispersed in PEG (oxSG-PEG) was current within the lungs at 1 day (D1), with accumulation lowering to about 5% of the ID at 90 days (D90). About 70-80% of the IDs of each oxSG-BSA and oxSG-PEG have been current within the liver at D1; by D90, about 15% of the IDs have been cleared slowly (oxSG-BSA) or quickly (oxSG-PEG). Within the spleen, about 7% of the IDs of each oxSG-BSA and oxSG-PEG have been current in any respect time factors.

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The toxicities of oxSG-BSA and oxSG-PEG have been comparable: no apparent indicators of irritation have been noticed on histological assessments of the lungs, liver, and spleen and on measurements of cytokine exercise in blood plasma and tissue lysates. Concentrations of aspartate transaminase barely elevated at a while factors in blood plasma, suggesting that oxSG-BSA and oxSG-PEG have been barely hepatoxic. Taken collectively, these outcomes indicated that the dispersants had restricted impact on the biodistribution and toxicity of oxSGs.

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