700-75-4Relevant academic research and scientific papers
Dirhodium-Catalyzed Chemo-and Site-Selective C-H Amidation of N, N-Dialkylanilines
Chen, Gong,Arai, Kenta,Morisaki, Kazuhiro,Kawabata, Takeo,Ueda, Yoshihiro
supporting information, p. 728 - 732 (2021/01/18)
A method for dirhodium-catalyzed C(sp 3)-H amidation of N, N-dimethylanilines was developed. Chemoselective C(sp 3)-H amidation of N-methyl group proceeded exclusively in the presence of C(sp 2)-H bonds of the electron-rich aromatic ring. Site-selective C(sp 3)-H amidation proceeded exclusively at the N-methyl group of N-methyl-N-Alkylaniline derivatives with secondary, tertiary, and benzylic C(sp 3)-H bonds α to a nitrogen atom.
Mn-Catalyzed Selective Double and Mono-N-Formylation and N-Methylation of Amines by using CO2
Huang, Zijun,Jiang, Xiaolin,Zhou, Shaofang,Yang, Peiju,Du, Chen-Xia,Li, Yuehui
, p. 3054 - 3059 (2019/04/10)
Functionalization of amines by using CO2 is of fundamental importance considering the abundance of amines and CO2. In this context, the catalytic formylation and methylation of amines represent convenient and successful protocols for selective CO2 utilization as a C1 building block. This study represents the first example of selective catalytic double N-formylation of aryl amines by using a dinuclear Mn complex in the presence of phenylsilane. This robust system also allows for selective formylation and methylation of amines under a range of conditions.
Synergistic catalysis of Cu+/Cu0 for efficient and selective N-methylation of nitroarenes with para-formaldehyde
Dong, Xiaosu,Wang, Zhaozhan,Yuan, Youzhu,Yang, Yong
, p. 304 - 313 (2019/07/02)
In this paper, an inexpensive heterogeneous copper nanoparticles catalyst derived from CuAl-layered double hydroxide via an in situ topotactic transformation process was developed. Cu nanoparticles with uniform size were homogeneously dispersed on amorphous Al2O3 with strong metal-support interaction. Characterization results reveals that the Cu0 and Cu+ were simultaneously formed with Cu+ species as the dominant sites on the surface during the reduction process. The resultant catalyst Cu/Al2O3 demonstrates high catalytic activity, selectivity and durability for the reductive N-methylation of easily available nitroarenes in a cost-efficient, environmentally friendly and cascade manner. A broad spectrum of nitroarenes could be efficiently N-methylated to their corresponding N,N-dimethyl amines with good compatibility of various functional groups. The protocol is also applicable for the late-stage functionalization of biologically and pharmaceutically active nitro molecules. A structure-function relationship discloses that Cu0 and Cu+ sites on the surface pronouncedly boosts the reaction efficiency in a synergistic manner, in which Cu0 could facilitate H2 production and N-methylation of anilines, while Cu+ is considerably more active and participates in the overall process of the selective N-methylation of nitroarenes. Moreover, the catalyst also showed a strong stability and could be easily separated for successive reuses without an appreciable loss in activity and selectivity.
Diverse catalytic reactivity of a dearomatized PN3P?-nickel hydride pincer complex towards CO2 reduction
Li, Huaifeng,Gon?alves, Théo P.,Zhao, Qianyi,Gong, Dirong,Lai, Zhiping,Wang, Zhixiang,Zheng, Junrong,Huang, Kuo-Wei
supporting information, p. 11395 - 11398 (2018/10/20)
A dearomatized PN3P?-nickel hydride complex has been prepared using an oxidative addition process. The first nickel-catalyzed hydrosilylation of CO2 to methanol has been achieved, with unprecedented turnover numbers. Selective methylation and formylation of amines with CO2 were demonstrated by such a PN3P?-nickel hydride complex, highlighting its versatile functions in CO2 reduction.
N-Alkylation of Aniline and Its Derivatives by Alcohols in the Presence of Copper Compounds
Bayguzina,Musina, Ch. F.,Khusnutdinov
, p. 1652 - 1659 (2019/02/12)
N-Alkyl- and N,N-dialkyl-substituted anilines were obtained in the reaction of aniline and its derivatives with primary and secondary alcohols in the presence of catalysts CuCl2·2H2O, CuBr2 and halomethanes as promoters.
Deoxygenation of tertiary amine N-oxides under metal free condition using phenylboronic acid
Gupta, Surabhi,Sureshbabu, Popuri,Singh, Adesh Kumar,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
supporting information, p. 909 - 913 (2017/02/15)
A simple and efficient method for the deoxygenation of amine N-oxides to corresponding amines is reported using the green and economical reagent phenylboronic acid. Deoxygenation of N,N-dialkylaniline N-oxides, trialkylamine N-oxides and pyridine N-oxides were achieved in good to excellent yields. The reduction susceptible functional groups such as ketone, amide, ester and nitro groups are well tolerated with phenylboronic acid during the deoxygenation process even at high temperature. In addition, an indirect method for identification and quantification of tert-amine N-oxide is demonstrated using UV–Vis spectrometry which may be useful for drug metabolism studies.
Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals
Fava, Eleonora,Millet, Anthony,Nakajima, Masaki,Loescher, Sebastian,Rueping, Magnus
supporting information, p. 6776 - 6779 (2016/06/09)
Visible-light-mediated photoredox-catalyzed aldimine-aniline and aldehyde-aniline couplings have been realized. The reductive single electron transfer (SET) umpolung of various carbonyl derivatives enabled the generation of intermediary ketyl and α-amino radical anions, which were utilized for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols. Anilines can be coupled with aldimines or aldehydes in a visible-light-mediated photoredox-catalyzed process. Reductive single electron transfer (SET) umpolung of the carbonyl derivatives leads to the generation of intermediary ketyl and α-amino radical anions, which were used for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols.
Room-temperature copper-catalyzed arylation of dimethylamine and methylamine in neat water
Wang, Deping,Kuang, Daizhi,Zhang, Fuxing,Yang, Chunlin,Zhu, Xiaoming
supporting information, p. 714 - 718 (2015/03/18)
The first room-temperature copper-catalyzed arylations of dimethylamine and methylamine in neat water have been developed. Using a combination of CuI and 6,7-dihydroquinolin-8(5 H)-one oxime as catalyst, dimethylamine is arylated with various aryl halides to give the corresponding products in good to excellent yields. Further, this catalysis enables the selective arylation of methylamine to afford the high yields of monoarylated methylamines as the sole products.
Light-promoted N,N-dimethylation of amine and nitro compound with methanol catalyzed by Pd/TiO2 at room temperature
Zhang, Lina,Zhang, Yan,Deng, Youquan,Shi, Feng
, p. 14514 - 14521 (2015/03/05)
A series of TiO2 supported nano-Pd catalysts (Pd/TiO2) were prepared and used for the N,N-dimethylation of different amines and nitro compounds with methanol under UV irradiation at room temperature. A wide range of N,N-dimethyl amines were one-pot synthesized with up to 98% by applying aliphatic secondary amines, aromatic primary amines, aliphatic primary amines and aromatic nitro compounds as starting materials. It is noteworthy that up to 90% yield of 4-chloro-N,N-dimethylaniline was obtained by adjusting the Pd loadings on the TiO2 and the dehalogenation reaction was inhibited. Finally, a reaction mechanism is discussed, involving PhN = CH2 and PhNHCH3 as reaction intermediates.
Iron-catalyzed aryl-aryl cross coupling route for the synthesis of 1-(2-amino)-phenyl)dibenzo[b,d]furan-2-ol derivatives and their biological evaluation
Chiranjeevi, Barreddi,Koyyada, Ganesh,Prabusreenivasan,Kumar, Vanaja,Sujitha, Pombala,Kumar, C. Ganesh,Sridhar,Shaik, Saida,Chandrasekharam, Malapaka
, p. 16475 - 16485 (2013/09/23)
Naturally occurring dibenzofuran motifs represent promising lead structures for the development of novel antimycobacterial agents. Prompted by our recent development of cross dehydrogenative coupling using iron catalysis, we extended our strategy to synthesize 14 novel anilinodibenzofuranols and they were explored for anti-tubercular and cytotoxic activities. Consistent with our hypothesis, DBF-3, 14 and 16 exhibited promising activity against two strains (M. tuberculosis H37Rv and the clinical S, H, R, and E resistant isolate), while DBF-13, 18 exhibited selective inhibitory activity only against the clinical S, H, R and E resistant isolate. However, the compounds DBF-4 and DBF-8 showed promising and selective antitumor activity against the tested cancer cell lines. The Royal Society of Chemistry 2013.
