55197-79-0Relevant academic research and scientific papers
Reductive Alkylation of Azides and Nitroarenes with Alcohols: A Selective Route to Mono- And Dialkylated Amines
Borthakur, Ishani,Maji, Milan,Joshi, Abhisek,Kundu, Sabuj
, p. 628 - 643 (2021/12/27)
Herein, we demonstrated an efficient protocol for reductive alkylation of azides/nitro compounds via a borrowing hydrogen (BH) method. By following this protocol, selective mono- and dialkylated amines were obtained under mild and solvent-free conditions. A series of control experiments and deuterium-labeling experiments were performed to understand this catalytic process. Mechanistic studies suggested that the Ir(III)-H was the active intermediate in this reaction. KIE study revealed that the breaking of the C-H bond of alcohol might be the rate-limiting step. Notably, this solvent-free strategy disclosed a high TON of around 5600. Based on kinetic studies and control experiments, a metal-ligand cooperative mechanism was proposed.
Copper-catalyzed electrophilic amination using: N -methoxyamines
Fukami, Yutaro,Wada, Takamasa,Meguro, Tatsuhiko,Chida, Noritaka,Sato, Takaaki
supporting information, p. 5486 - 5489 (2016/07/06)
Copper-catalyzed electrophilic amination of a triarylboroxin using an N-methoxyamine to give quick access to a variety of anilines was reported. The reaction was especially useful for syntheses of functionalized anilines when combined with our previously reported nucleophilic addition to N-methoxyamides.
Method of producing higher amine (by machine translation)
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Paragraph 0048; 0091; 0103, (2016/10/08)
PROBLEM TO BE SOLVED: To provide a method of producing a secondary or tertiary higher amine. SOLUTION: The method of producing a higher amine comprises allowing a primary or secondary amine to react with an alcohol in the presence of at least one species of hydrogen halide selected from hydrogen chloride, hydrogen bromide and hydrogen iodide, or in the presence of a compound capable of producing a hydrogen halide (such as 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-chloride). If the raw material amine is a primary amine, a secondary higher amine and a tertiary higher amine can be produced. If the raw material amine is a secondary amine, a tertiary higher amine can be produced. COPYRIGHT: (C)2012,JPO&INPIT
Concise synthesis of aromatic tertiary amines via a double Petasis-borono Mannich reaction of aromatic amines, formaldehyde, and organoboronic acids
Wang, Jiayi,Li, Pinzhen,Shen, Qiaoying,Song, Gonghua
supporting information, p. 3888 - 3891 (2014/07/08)
A simple and efficient strategy to construct aromatic tertiary amines via a double Petasis-borono Mannich reaction of aromatic amines, formaldehyde, and organoboronic acids has been developed. The transformation provides a useful method for the synthesis of amine derivatives.
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.
Synthesis of benzidine derivatives via FeCl3·6H 2O-promoted oxidative coupling of anilines
Ling, Xuege,Xiong, Yan,Huang, Ruofeng,Zhang, Xiaohui,Zhang, Shuting,Chen, Changguo
supporting information, p. 5218 - 5226 (2013/07/25)
Under open-flask conditions in the presence of commercially available FeCl3·6H2O, N,N-disubstituted anilines can be converted into diversely functionalized benzidines with yields of up to 99%. Oxidative coupling was extended to N-monosubstituted anilines, and the method was applied to the efficient preparation of 6,6′-biquinoline. Mechanistic investigations have also been performed to explain the observed reactivities.
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
Direct one-pot reductive N-alkylation of nitroarenes by using alcohols with supported gold catalysts
Tang, Chun-Hong,He, Lin,Liu, Yong-Mei,Cao, Yong,He, He-Yong,Fan, Kang-Nian
supporting information; experimental part, p. 7172 - 7177 (2011/09/15)
Gold standard support! The direct reductive mono- or di-N-alkylation of aromatic nitro compounds with alcohols, using a hydrogen-borrowing strategy, was efficiently promoted by a ligand-free titania-supported gold catalyst system (see scheme). A variety of nitroarenes were selectively converted into the corresponding secondary or tertiary amines in good to excellent yields without any co-catalysts, such as bases and stabilizing ligands. Copyright
Selective N-alkylation of amines with alcohols by using non-metal-based acid-base cooperative catalysis
Du, Ya,Oishi, Shunsuke,Saito, Susumu
supporting information; experimental part, p. 12262 - 12267 (2011/11/29)
Learning to cooperate: A straightforward method for the selective N-mono- and dialkylation of amines with alcohols by means of non-metal-based catalysis promoted by TAPC is reported (see scheme). Selectivity of the N-mono- and dialkylation, substrate scope and functional-group tolerance are highlighted with respect to each amine (1° and 2°; aromatic and aliphatic) and alcohol (1°, 2° and 3°; benzylic and aliphatic) component. Copyright
Ruthenium-catalyzed tertiary amine formation from nitroarenes and alcohols
Feng, Chao,Liu, Yong,Peng, Shengming,Shuai, Qi,Deng, Guojun,Li, Chao-Jun
supporting information; experimental part, p. 4888 - 4891 (2010/12/25)
A highly selective ruthenium-catalyzed C-N bond formation was developed by using the hydrogen-borrowing strategy. Various tertiary amines were obtained efficiently from nitroarenes and primary alcohols. The reaction tolerates a wide range of functionalities. A tentative mechanism was proposed for this direct amination reaction of alcohols with nitroarenes.
