4409-84-1

Upstream product

• 932-31-0 ortho-tolylmagnesium bromide 
• 758-12-3 deuteroacetic acid 
• 6699-93-0 (2-methylphenyl)lithium 
• 91996-53-1 l'alcool benzylique o-deuterie 
• 599-00-8 trifluoroacetic acid-d₁ 
• 811-98-3 d⁽⁴⁾-methanol 
• 108-88-3 toluene 
• 95-46-5 2-methylphenyl bromide 

Downstream Products

• 4551-39-7 2-deuteriobenzoic acid 
• 116569-21-2 <2-D₁>Benzylchlorid 
• 66154-03-8 2-deuteriobenzaldehyde 
• 857001-55-9 1-bromomethyl-2-deuterio-benzene 
• 50535-19-8 2-deuterobenzylidenedichloride 
• 108-88-3 toluene 
• 90625-40-4 trans-2,2'-dideuterio-stilbene 
• 1443788-15-5 2-deuterio-N-(8-quinolinyl)benzamide 
• 1311147-16-6 2-benzyl-3-tert-butylisoindolin-1-one 
• 1311147-24-6 2-benzyl-3-tert-butyl-7-deuterioisoindolin-1-one 
• 1311147-09-7 N-benzyl-N-(1-methoxy-2,2-dimethylpropyl)-o-deuteriobenzamide 
• 43019-96-1 d₂-benzoyl chloride 
• 91996-53-1 l'alcool benzylique o-deuterie 

Relevant academic research and scientific papers

Nickel-mediated C(sp2)-H amidation in synthesis of secondary sulfonamides via sulfonyl azides as amino source

In this paper, Ni(II)- Catalyzed ortho-amidation of C(sp2)-H bond with sulfonyl azides directed by (quinolin-8-yl) amine (AQ-amine) is described. The method provides a straightforward method for the synthesis of sulfonamides from available sulfonyl azides via the transition-metal-catalyzed C(sp2)-N bond forming reaction. The amidation reactions exhibit high functional group compatibility, which might proceed a Ni(III)/Ni(I) catalytic cycle. We also applied sulfonamide compound in OLEDs, which exhibits the certain application potential in OLEDs field.

Metal-Free sp2-C-H Borylation as a Common Reactivity Pattern of Frustrated 2-Aminophenylboranes

C-H borylation is a powerful and atom-efficient method for converting affordable and abundant chemicals into versatile organic reagents used in the production of fine chemicals and functional materials. Herein we report a facile C-H borylation of aromatic and olefinic C-H bonds with 2-aminophenylboranes. Computational and experimental studies reveal that the metal-free C-H insertion proceeds via a frustrated Lewis pair mechanism involving heterolytic splitting of the C-H bond by cooperative action of the amine and boryl groups. The adapted geometry of the reactive B and N centers results in an unprecedentently low kinetic barrier for both insertion into the sp2-C-H bond and intramolecular protonation of the sp2-C-B bond in 2-ammoniophenyl(aryl)- or -(alkenyl)borates. This common reactivity pattern serves as a platform for various catalytic reactions such as C-H borylation and hydrogenation of alkynes. In particular, we demonstrate that simple 2-aminopyridinium salts efficiently catalyze the C-H borylation of hetarenes with catecholborane. This reaction is presumably mediated by a borenium species isoelectronic to 2-aminophenylboranes.

Divergence between organometallic and single-electron-transfer mechanisms in copper(II)-mediated aerobic c-h oxidation

Copper(II)-mediated C-H oxidation is the subject of extensive interest in synthetic chemistry, but the mechanisms of many of these reactions are poorly understood. Here, we observe different products from CuII-mediated oxidation of N-(8-quinoli

Nickel(0)-catalyzed cyclization of N -benzoylaminals for isoindolinone synthesis

A nickel(0) catalyst effectively mediates the cyclization of N-benzoyl aminals in the presence of a stoichiometric Lewis acid. This method enables preparation of a variety of isoindolinones with substitution on the benzoyl fragment and C-3 carbon. This reaction likely proceeds via an α-amidoalkylnickel(II) intermediate, which then may cyclize via either an electrophilic aromatic substitution or an insertion pathway.

USE OF ARYL CHLORIDES IN PALLADIUM-CATALYZED C-H BOND FUNCTIONALIZATION

A one-step method for efficiently converting carbon-hydrogen bonds into carbon-carbon bonds using chloroarenes and palladium catalysts is disclosed. This method allows faster introduction of complex molecular entities, a process that would otherwise require many more steps. This invention is particularly relevant for the organic synthesis of complex molecules such as, but not limited to, pharmacophores.

Two methods for direct ortho-arylation of benzoic acids

Two new palladium-catalyzed methods for the direct ortho-arylation of free benzoic acids have been developed. The first method employs stoichiometric silver acetate for iodide removal, aryl iodide as the coupling partner, and acetic acid solvent. This method is applicable to the arylation of electron-rich to moderately electron-poor benzoic acids and tolerates chloride and bromide substituents on both coupling partners. The second method involves the use of aryl chloride, cesium carbonate base, n-butyl-di-1-adamantylphosphine ligand, and DMF solvent and is suitable for both electron-rich and electron-poor benzoic acids. Mechanistic studies of the second method point to the heterolytic C-H bond cleavage as the rate-determining step.

Mechanistical studies on C-H activation reactions of benzaldimines using selectively deuterated ligands: Synthesis and crystal structures of [μ2-η3-(R)N-CH 2-C=C-C(H)=C(H)-C(H)=C(H)]Fe2(CO)6

The reaction of Fe2(CO)9 with imine ligands derived from benzaldehyde leads to the formation of dinuclear iron cluster compounds of the general formula [μ2-η3-N-CH 2-C=C-C(H)=C(H)-C(H)=C(H)]Fe2(CO)6 by a C-H activation/1,3-hydrogen shift reaction sequence. Six cluster compounds with alkyl and aryl substituents bound to nitrogen have been synthesised and characterised, five of them also by means of X-ray crystallography. The mechanism of the reaction has been investigated by the use of ligands being selectively deuterated in the 2-position. By several NMR experiments including deuterium spectra it can be demonstrated that the hydrogen/deuterium atom of the activated aromatic C-H bond is transferred to the former imine carbon atom producing a methylene group instead and that this reaction strictly follows an intramolecular pathway.

Structural dependence of isotope effects in 1H and 13C nuclear magnetic resonance spectra of the trans-N-benzylideneaniline imino group

Deutrium- and 15N-induced isotope effects on 1H and 13C chemical shifts of the imino moiety of 16 trans-N-benzylideneaniline (tBA) isotopomers were determined and analysed. These effects appear to be a sensitive probe of m

1,2,4,6-CYCLOHEPTATETRAENE: THE KEY INTERMEDIATE IN ARYLCARBENE INTERCONVERSIONS AND RELATED C7H6 REARRANGEMENTS

Thermolysis or photolysis of phenyldiazomethane (2) produces phenylmethylene (3), which ring-expands to give 1,2,4,6-cycloheptatetraene (6).Spectroscopic and chemical evidence rule out bicyclo(4.1.0)hepta-2,4,6-triene (4), cycloheptatrienylidene (5), and bicyclo(3.2.0)hepta-1,3,6-triene (11) intermediates.The strained allene in cycloheptatetraene (6) exhibits infrared absorption at 1824 and 1816 cm-1.Deuterium substitution produces the expected 10-cm-1 shift in the allene absorption.Fluorine or chlorine substitution substantially enhances the allene absorption intensity.Deuterium labeling studies reveal that the intramolecular chemistry of cycloheptatetraene (6) involves reversible thermal or photochemical equilibriation with phenylmethylene (3).The intermolecular chemistry of 6 involves dimerization.At temperatures as low as 10 K, 6 forms a labile (2+2) dimer,7, which undergoes thermally allowed, electrocyclic ring opening to give heptafulvalene (8) upon warming to room temperature.The rearrangements of 7-acetoxynorbornadiene (9), 2-diazobicyclo(3.2.0)hepta-3,6-diene (31), and 8-diazobicyclo(2.2.2)octa-2,5-dien-7-one (33) all involve cycloheptatetraene (6) intermediates.

INTRAMOLECULAR DEUTERIUM ISOTOPE EFFECTS IN THE META PHOTOCYCLOADDITION OF AROMATIC COMPOUNDS TO ALKENES.

The effect of substitution of hydrogen by deuterium in some aromatic compounds on product distributions in the meta photocycloaddition to alkenes was investigated.The isotope effects found are in agreement with a polar mechanism.