23824-51-3Relevant academic research and scientific papers
Heterogeneous Ru/TiO2for hydroaminomethylation of olefins: multicomponent synthesis of amines
An, Jinghua,Gao, Zhuyan,Wang, Yehong,Zhang, Zhixin,Zhang, Jian,Li, Lu,Tang, Bo,Wang, Feng
supporting information, p. 2722 - 2728 (2021/04/21)
Synthesizing aminesviathe hydroaminomethylation (HAM) reaction of olefins, a multicomponent reaction, has been regarded as one of the most attractive methods compared with the traditional methods considering the atom economy and environmental friendliness. However, the use of homogeneous catalysts, complex ligands containing diphosphine or nitrogen, and base or acid additives has severely hampered the utilization of these methods. Herein, an efficient heterogeneous Ru/TiO2-catalyzed HAM reaction of olefins is developed without any additives. Various amines, including secondary and tertiary amines, can be successfully obtained from olefins including aromatic and aliphatic olefins. Systematic studies demonstrate the lower electron density of Ruδ+and the higher number of acid sites of Ru/TiO2, leading to the high HAM reaction activity of olefins. Most importantly, nitrobenzene derivatives can also be transformed to the corresponding products over Ru/TiO2in excellent yields.
Iron-Catalyzed Regioselective α-C-H Alkylation of N-Methylanilines: Cross-Dehydrogenative Coupling between Unactivated C(sp3)-H and C(sp3)-H Bonds via a Radical Process
Li, Ze-Lin,Sun, Kang-Kang,Wu, Peng-Yu,Cai, Chun
, p. 6830 - 6839 (2019/06/14)
The iron-catalyzed α-C-H alkylation of N-methylanilines without any directing group by cross-dehydrogenative coupling between unactivated C(sp3)-H and C(sp3)-H bonds has been established for the first time, which provides a good complement to C(sp3)-H activation reactions and expands the field of Fe-catalyzed C-H functionalizations. Many different C(sp3)-H bonds in cyclic alkanes, cyclic ethers, and toluene derivatives can be used as coupling partners. Mechanistic investigations including the radical reaction process, the main role of various reagents, and the kinetic isotope effect experiment were also described.
Hydroaminoalkylation of sterically hindered alkenes with: N, N -dimethyl anilines using a scandium catalyst
Su, Jianhong,Zhou, Yiqun,Xu, Xin
supporting information, p. 2013 - 2019 (2019/02/20)
An atom- and step-economical C(sp3)-H addition of N,N-dimethyl anilines to various sterically demanding 1,1- and 1,2-disubstituted alkenes has been achieved by using a simple β-diketiminato ligand supported scandium dialkyl complex in combinati
Synthetic β-Cyclodextrin Dimers for Squaraine Binding: Effect of Host Architecture on Photophysical Properties, Aggregate Formation and Chemical Reactivity
Chaudhuri, Sauradip,Verderame, Molly,Mako, Teresa L.,Bandara, Y. M. Nuwan D. Y.,Fernando, Ashvin I.,Levine, Mindy
supporting information, p. 1964 - 1974 (2018/05/15)
Reported herein is the synthesis and application of three novel β-cyclodextrin dimer hosts for the complexation of near infrared (NIR) squaraine dyes in aqueous solution. A series of eight different N-substituted N-methyl anilino squaraine dyes with variable terminal groups are investigated, with an optimal n-hexyl-substituted squaraine guest demonstrating binding constants orders of magnitude higher than the other squaraine–host combinations and comparable to literature-reported systems. Moreover, hydrophobic complexation of the squaraine dyes with the β-cyclodextrin dimer hosts causes drastic changes in the squaraine's photophysical properties, propensity for aggregation and susceptibility to hydrolytic decay.
Catalytic N-Alkylation of Amines Using Carboxylic Acids and Molecular Hydrogen
Sorribes, Iván,Cabrero-Antonino, Jose R.,Vicent, Cristian,Junge, Kathrin,Beller, Matthias
supporting information, p. 13580 - 13587 (2015/11/10)
A convenient, practical and green N-alkylation of amines has been accomplished by applying readily available carboxylic acids in the presence of molecular hydrogen. Applying an in situ formed ruthenium/triphos complex and an organic acid as cocatalyst, a broad range of alkylated secondary and tertiary amines are obtained in good to excellent yields. This novel method is also successfully applied for the synthesis of unsymmetrically substituted N-methyl/alkyl anilines through a direct three-component coupling reaction of the corresponding amines, carboxylic acids, and CO2 as a C1 source.
Mild and selective Et2Zn-catalyzed reduction of tertiary amides under Hydrosilylation conditions
Kovalenko, Oleksandr O.,Volkov, Alexey,Adolfsson, Hans
, p. 446 - 449 (2015/03/05)
Diethylzinc (Et2Zn) can be used as an efficient and chemoselective catalyst for the reduction of tertiary amides under mild reaction conditions employing cost-effective polymeric silane (PMHS) as the hydride source. Crucial for the catalytic activity was the addition of a substoichiometric amount of lithium chloride to the reaction mixture. A series of amides containing different additional functional groups were reduced to their corresponding amines, and the products were isolated in good-to-excellent yields.
A versatile method for the N,N-dialkylation of aromatic amines via Grignard reactions on N,N-bis(benzotriazolylmethyl)arylamines
Katritzky, Alan R.,Rachwal, Stanislaw,Wu, Jing
, p. 456 - 463 (2007/10/02)
Grignard reactions of N,N-bis(benzotriazolylmethyl)arylamines afford the corresponding N,N-dialkylarylamines in high yields.Electron-releasing substituents on the aryl ring facilitate the reaction.Arylamines are N,N-dialkylated with two different alkyl groups by a stepwise procedure: N-benzotriazolylmethylation of an amine followed by a Grignard reaction to introduce the first alkyl group, and repetition of the same procedure to introduce the second alkyl group.Grignard reagents derived from 1,4-dihalobutane, upon reaction with N,N-bis(benzotriazolylmethyl)arylamines, give the corresponding N-aryl-hexahydroazepines together with acyclic products.
