56511-50-3Relevant academic research and scientific papers
ARYLATION OF ALIPHATIC AMINES
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Page/Page column 27; 28, (2017/09/07)
The invention relates to a method for arylation of amines, such as aliphatic amines by reaction of aryl-halogens, e.g. chloro- or fluorobenzene derivatives without strongly electron withdrawing substituents in the presence of a strong base.
Mechanism and Scope of Base-Controlled Catalyst-Free N-Arylation of Amines with Unactivated Fluorobenzenes
Borch Jacobsen, Christian,Meldal, Morten,Diness, Frederik
supporting information, p. 846 - 851 (2017/02/05)
A general method for transition metal-free N-arylation of amines has been developed. Mechanistic studies have revealed that the ability of the base to facilitate the desired amination without promoting unwanted side reactions is the guiding factor. By employing lithium bis(trimethylsilyl)amide as a base the resultant deprotonated amines readily react with a range of unactivated fluorobenzene derivatives. This new arylation method is utilized for the simple two-step synthesis of the antidepressant Vortioxetine.
Selective catalytic Hofmann: N -alkylation of poor nucleophilic amines and amides with catalytic amounts of alkyl halides
Xu, Qing,Xie, Huamei,Zhang, Er-Lei,Ma, Xiantao,Chen, Jianhui,Yu, Xiao-Chun,Li, Huan
supporting information, p. 3940 - 3944 (2016/07/21)
Using only catalytic amounts of alkyl halides in the reactions of poor nucleophilic amines/amides and alcohols led to a selective Hofmann N-alkylation reaction catalytic in alkyl halides, providing a practical and efficient method for the practical synthesis of mono- or di-alkylated amines/amides in high selectivities. This new method avoids the use of large amounts of bases, alkyl halides, and solvents, and generates water as the only byproduct. Preliminary mechanistic studies showed that alkyl halides are key intermediates/catalysts regeneratable in the reaction cycle.
Copper-Catalyzed Electrophilic Amination of Organoaluminum Nucleophiles with O -Benzoyl Hydroxylamines
Zhou, Shuangliu,Yang, Zhiyong,Chen, Xu,Li, Yimei,Zhang, Lijun,Fang, Hong,Wang, Wei,Zhu, Xiancui,Wang, Shaowu
, p. 6323 - 6328 (2015/06/30)
A copper-catalyzed electrophilic amination of aryl and heteroaryl aluminums with N,N-dialkyl-O-benzoyl hydroxylamines that affords the corresponding anilines in good yields has been developed. The catalytic reaction proceeds very smoothly under mild conditions and exhibits good substrate scope. Moreover, the developed catalytic system is also well suited for heteroaryl aluminum nucleophiles, providing facile access to heteroaryl amines.
SiO2-Cu2O: An efficient and recyclable heterogeneous catalyst for N-benzylation of primary and secondary amines
Gupta, Manjulla,Paul, Satya,Gupta, Rajive
, p. 444 - 450 (2014/04/03)
A mild, effective, and selective procedure is reported for the mono N-benzylation and N,N-dibenzylation of primary amines as well as mono N-benzylation of secondary amines using silica-supported copper(I) oxide in water. The silica-supported Cu2O was generated in situ by the reaction of Fehling solution and glucose at 100 C onto activated silica. The catalyst was filtered, washed with water, and oven-dried, and was characterized by Fourier transform infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, transmission electron microscopy, and atomic absorption spectroscopy. The prepared Cu2O-SiO2 was found to be thermally stable up to 325 C. The copper was uniformly distributed onto the surface of the silica, and the mean particle diameter was 7 nm. The catalyst served as a selective heterogenous catalyst for the N-benzylation of primary and secondary amines. The catalyst is recyclable and was used effectively upto fifth run without a significant loss of catalytic activity. Various reaction solvents including water, acetonitrile, and toluene were screened for N-benzylation of amines, and the success of the aqueous system highlights the low environmental impact of the procedure.
Insertion of arynes into the carbon-oxygen double bond of amides and its application into the sequential reactions
Yoshioka, Eito,Miyabe, Hideto
experimental part, p. 179 - 189 (2012/02/15)
The reaction of arynes, generated from ortho-(trimethylsilyl)aryl triflates, with the CO bond of formamides gave salicylaldehyde derivatives via the formation of formal [2+2] adducts. The sequential transformation of arynes into ortho-disubstituted arenes, o-aminoalkylphenols or o-hydroxyalkylphenols, was achieved by one-pot procedure using dialkylzincs.
Para-selective gold-catalyzed direct alkynylation of anilines
Brand, Jonathan P.,Waser, Jerome
supporting information; experimental part, p. 744 - 747 (2012/04/10)
A method for the para-selective alkynylation of anilines is reported using AuCl as catalyst and triisopropylsilylethynyl-1,2-benziodoxol-3(1H)-one (TIPS-EBX) as an electrophilic acetylene equivalent. Para-alkynyl anilines substituted at positions 2 or 3 w
Transition-metal-free electrophilic amination of arylboroxines
Xiao, Qing,Tian, Leiming,Tan, Renchang,Xia, Ying,Qiu, Di,Zhang, Yan,Wang, Jianbo
, p. 4230 - 4233 (2012/09/22)
A transition-metal-free strategy to construct C(sp2)-N bonds using arylboroxines and O-benzoyl hydroxylamines as coupling partners has been developed. This transformation provides a useful method to access various aromatic amines.
A novel (2,2-diarylvinyl)phosphine/palladium catalyst for effective aromatic amination
Suzuki, Ken,Hori, Yoji,Nishikawa, Takenobu,Kobayashi, Tohru
, p. 2089 - 2091 (2008/09/18)
A new series of diarylvinylphosphine ligands was designed and synthesized. A catalyst system, consisting of the ligands and palladium species, effectively catalyzed the coupling reaction of aryl bromides and chlorides with amines to afford the corresponding products in good to excellent yields. The efficiency is likely derived from an interaction between the palladium center and the cisaryl moiety on the diarylvinylphosphine ligand stabilizing a catalytic intermediate during the coupling reaction.
Efficient total synthesis of (+)-curcuphenol via asymmetric organocatalysis
Kim, Sung-Gon,Kim, Jaehak,Jung, Heejung
, p. 2437 - 2439 (2007/10/03)
The catalytic enantioselective synthesis of (+)-curcuphenol is described herein. This approach involves the use of an organocatalytic alkylation of m-anisidine, a diazotation/Sandmeyer reaction of the amine and a Negishi-type coupling with dimethylzinc. T
