132540-71-7Relevant academic research and scientific papers
Preparation of diarylamines by the addition of 4-(N,N-dimethylamino)phenyllithium to nitroarenes
Yang, Tianle,Cho, Bongsup P.
, p. 7549 - 7552 (2003)
The addition of 4-(N,N-dimethylamino)phenyllithium to nitroarenes in THF (-78°C) affords the corresponding diarylamines in one-pot and the reaction appears to be general in scope. A 'nitroso'-based mechanism is proposed for this novel nitroreductive N-arylation reaction.
(DiMeIHeptCl)Pd: A Low-Load Catalyst for Solvent-Free (Melt) Amination
Semeniuchenko, Volodymyr,Sharif, Sepideh,Day, Jonathan,Chandrasoma, Nalin,Pietro, William J.,Manthorpe, Jeffrey,Braje, Wilfried M.,Organ, Michael G.
, p. 10343 - 10359 (2021/07/31)
(DiMeIHeptCl)Pd, a hyper-branched N-aryl Pd NHC catalyst, has been shown to be efficient at performing amine arylation reactions in solvent-free ("melt") conditions. The highly lipophilic environment of the alkyl chains flanking the Pd center serves as lubricant to allow the complex to navigate through the paste-like environment of these mixtures. The protocol can be used on a multi-gram scale to make a variety of aniline derivatives, including substrates containing alcohol moieties.
Evidence for "cocktail"-type catalysis in Buchwald-Hartwig reaction. A mechanistic study
Ananikov, Valentine P.,Boiko, Daniil A.,Burykina, Julia V.,Madiyeva, Malena,Minyaev, Mikhail E.,Prima, Darya O.
, p. 7171 - 7188 (2021/11/17)
The mechanism of the C-N cross-coupling reaction, catalyzed by palladium complexes with N-heterocyclic carbene ligands (Pd/NHC), was evaluated in detail at the molecular and nanoscale levels. For the first time, the formation of a "cocktail"-type catalytic system was proven for the Buchwald-Hartwig reaction. The unique ability of the Pd/NHC system to generate several types of catalytic centers (Pd complexes, clusters and nanoparticles) and the involvement of complementary pathways (homogeneous and heterogeneous) were discovered to take place in a "one pot"manner directly in the reaction vessel. Access to various catalytic centers from a single and readily available Pd/NHC complex is the key to designing a universal catalytic system with adaptive tuning capability. This journal is
Nickel-catalyzed synthesis of diarylamines via oxidatively induced C-N bond formation at room temperature
Ilies, Laurean,Matsubara, Tatsuaki,Nakamura, Eiichi
supporting information, p. 5570 - 5573,4 (2012/12/12)
A nickel-catalyzed oxidative coupling of zinc amides with organomagnesium compounds selectively produces diarylamines under mild reaction conditions, with tolerance for chloride, bromide, hydroxyl, ester, and ketone groups. A diamine is bis-monoarylated. A bromoaniline undergoes N-arylation followed by Kumada-Tamao-Corriu coupling in one pot. The reaction may proceed via oxidatively induced reductive elimination of a nickel species.
Mechanism of the Reaction of Carbon and Nitrogen Nucleophiles with the Model Carcinogens O-Pivaloyl-TV-arylhydroxylamines: Competing SN2 Substitution and SN1 Solvolysis
Helmick, John S.,Martin, Kristy A.,Heinrich, Julie L.,Novak, Michael
, p. 3459 - 3466 (2007/10/02)
The reaction of N,N-dimethylaniline (4) and aniline (5) with the O-pivaloyl-N-arylhydroxylamines 1a-f) in MeOH exhibits second-order kinetics and generates products of nucleophilic attack on the nitrogen of the hydroxylamine derivative. The characteristics of this reaction are not consistent with a nitrene or SET mechanism, an SN1 reaction with rate-limiting attack of the nucleophile, or nucleophile-assisted ionization. The only mechanism consistent with the available data, including substituent effects (ρ+ ≈ -3.0), cyclic voltammetry results, and product identifications, is an SN2 process. This reaction occurs in competition with an SN1 solvolysis that shows significant substituent dependence (ρ+ = -8.5). The reaction of 1 with 5 generates products of nucleophilic attack by both carbon (8, 9) and nitrogen (10). Competitive attack by carbon apparently occurs because of transition-state stabilization caused by the incipient C-N bond. The successful competition of the 8N2 reactions with SN1 solvolysis for the esters 1a and 1b, which are similar in reactivity to the putative carcinogens 2a-c, indicates that certain adducts isolated from in vivo experiments, including 3, may be formed via SN2 mechanisms.
Stabilization of unsaturated carboxylic acid esters with mixtures of polyalkylene-amines and arylenediamines
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, (2008/06/13)
A method of inhibiting polymerization of unsaturated carboxylic acid esters and improved unsaturated carboxylic acid ester compositions are described. The method comprises, and the compositions are prepared by, incorporating into the ester composition a combination comprising polyalkyleneamine and arylenediamine of the formula STR1 in which X is hydrogen, chloro, trichloromethyl, trifluoromethyl, nitro, lower alkyl, lower alkoxy or phenoxy, R is hydrogen or alkyl, and R1 is alkyl or phenyl or R and R1 together with the nitrogen atom is a heterocycle selected from the group consisting of pyrrolidinyl, 2,5-dimethyl pyrrolidinyl, piperidino and hexahydro-1H-azepin-1-yl.
