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Upstream product

• 2156-71-0 N-chloropiperidine 
• 34696-73-6 3,5-dimethyphenylmagnesium bromide 
• 110-89-4 piperidine 
• 108-68-9 3,5-Dimethylphenol 
• 1123-09-7 3,5-dimethyl-2-cyclohexen-1-one 
• 766-09-6 1-ethyl-piperidine 
• 556-96-7 5-bromo-1,3-xylene 
• 111-24-0 1,5-dibromo-pentane 
• 108-69-0 3,5-dimethylaminoaniline 
• 773-01-3 2,4,6-trimethylpyrylium tetrafluoroborate 

Relevant academic research and scientific papers

Dipole Moments of Some N-Phenyl-substituted Derivatives of Pyrrolidine, Piperidine, Morpholine, and Thiomorpholine

Apparent dipole moments in benzene of various p-substituted N-phenyl derivatives of pyrrolidine, piperidine, morpholine, and thiomorpholine and of some analogous NN-diethylanilines have been determined.Vector moments along the bisector of angle CH2NCH2 and also in the direction of the major axis of the aromatic ring have been calculated for the parent compounds.The order of magnitude of the latter is N-phenylpyrrolidine>NN-diethylaniline>N-phenylpiperidine>N-phenylmorpholine>N-phenylthiomorpholine.The nature of the heterocycle does not greatly affect the additional moment, μ(add.), along the major axis of the aromatic ring, required to account for the moments of the p-substituted compounds.In each series of compounds, μ(add.) parallels the Hammett substituent constant, ?.

Catalytic Amination of Phenols with Amines

Given the wide prevalence and ready availability of both phenols and amines, aniline synthesis through direct coupling between these starting materials would be extremely attractive. Herein, we describe a rhodium-catalyzed amination of phenols, which provides concise access to diverse anilines, with water as the sole byproduct. The arenophilic rhodium catalyst facilitates the inherently difficult keto–enol tautomerization of phenols by means of π-coordination, allowing for the subsequent dehydrative condensation with amines. We demonstrate the generality of this redox-neutral catalysis by carrying out reactions of a large array of phenols with various electronic properties and a wide variety of primary and secondary amines. Several examples of late-stage functionalization of structurally complex bioactive molecules, including pharmaceuticals, further illustrate the potential broad utility of the method.

Pd-catalyzed synthesis of aryl amines via oxidative aromatization of cyclic ketones and amines with molecular oxygen

Pd-catalyzed intermolecular aerobic dehydrogenative aromatizations have been developed for the arylation of amines with nonaromatic ketones. Under optimized reaction conditions, primary and secondary amines are selectively arylated in good yields with cyclohexanones and 2-cyclohexen-1-ones in the presence of a Pd-catalyst under an atmosphere of molecular oxygen.

Direct base-assisted C-N bond formation between aryl halides and aliphatic tertiary amines under transition-metal-free conditions

Direct base-mediated amination of aryl halides with aliphatic tertiary amines via an aryne intermediate was developed under transition-metal-free conditions. This operationally simple C-N bond-coupling protocol could tolerate a variety of functionalized aryl halides as well as several aliphatic tertiary amines. Moreover, this environmentally benign process provides a new strategy for direct C-N bond formation.

Transition-metal-free electrophilic amination between aryl grignard reagents and N-chloroamines

In the presence of N,N,N′,N′-tetramethylethylenediamine (TMEDA) as an additive, easily prepared and handled N-chloroamines react with aryl Grignard reagents to give a variety of arylamines in good to excellent yields. Functional groups such as ester and nitrile are compatible under the reaction conditions (Figure Presented).

SYNTHESE DE N,N-DIALKYL-3,5-DIALKYL-ANILINES A PARTIR DES SELS DE TRIALKYL-2,4,6-PYRYLIUM

We have optimized through an experimental design the synthesis of N,N-diethyl-3,5-dimethylaniline from 2,4,6-trimethylpyrylium terafluoroborate (I) and diethylamine in a new reaction medium (acetonitrile/triethylamine).Optimal conditions have been applied with high yields to the synthesis of various 3,5-dimethylanilines derived from I and dimethylamine, morpholine, N-methylpiperazine, piperazine, dihexylamine, piperidine, and pyrrolidine respectively. 2-Alkyl-4,6-dimethylpyrylium tetrafluoroborates react regioselectively with diethylamine to afford N,N-diethyl-3-alkyl-5-methyl anilines under these conditions.