57818-33-4Relevant academic research and scientific papers
Achieving Aliphatic Amine Addition to Arylalkynes via the Lewis Acid Assisted Triazole-Gold (TA-Au) Catalyst System
Jia, Teng,Fan, Shengyu,Li, Fengmian,Ye, Xiaohan,Zhang, Wenke,Song, Zhiguang,Shi, Xiaodong
supporting information, p. 6019 - 6023 (2021/08/03)
Transition metal catalyzed intermolecular hydroamination of the arylalkynes with aliphatic amine is generally problematic due to the good coordination between amine and metal cation. With the combination of 1,2,3-triazole coordinated gold(I) catalyst (TA-Au) and Zn(OTf)2 cocatalyst, this challenging transformation was achieved with good to excellent yields and regioselectivity. Compared to previously reported methods, this approach offered an alternative catalyst system to achieve this fundamental chemical transformation with high efficiency and practical conditions.
Zirconium catalysed intermolecular hydroamination reactions of secondary amines with alkynes
Sun, Qiu,Wang, Yaorong,Yuan, Dan,Yao, Yingming,Shen, Qi
supporting information, p. 7633 - 7636 (2015/06/01)
An in situ generated cationic zirconium complex stabilized by an n-butylamine-bridged bis(phenolato) ligand has been developed to catalyse hydroamination reactions of secondary amines, which is the first example of group 4 metal based catalysts capable of
Palladium catalyzed animation of vinyl chlorides: A new entry to imines, enamines and 2-amino-1,3-butadienes
Barluenga, Jose,Fernandez, M. Alejandro,Aznar, Fernando,Valdes, Carlos
, p. 1400 - 1401 (2007/10/03)
Vinyl chlorides are employed for the first time in palladium catalyzed cross-coupling reactions with amines to furnish imines and enamines. The new methodology has been applied to the synthesis of 2-amino-1,3-butadienes, that could not be achieved from th
Palladium-Catalyzed Cross-Coupling Reactions of Amines with Alkenyl Bromides: A New Method for the Synthesis of Enamines and Imines
Barluenga, Jose,Fernandez, M. Alejandro,Aznar, Fernando,Valdes, Carlos
, p. 494 - 507 (2007/10/03)
The palladium-catalyzed cross-coupling reaction of alkenyl bromides with secondary and primary amines gives rise to enamines and imines, respectively. This new transformation expands the applicability of palladium-catalyzed C-N bond forming reactions (the Buchwald-Hartwig amination), which have mostly been applied to aryl halides. After screening of different ligands, bases, and solvents, the catalytic combination [Pd2(dba)3]/BINAP in the presence of NaOtBu in toluene gave the best results in the cross-coupling of secondary amines with 1-bromostyrene (dba=dibenzylideneacetone, BINAP=2,2′-bis(diphenylphosphino)-1,1′-binaphthyl). The corresponding enamines are obtained cleanly and in nearly quantitative yields. However, steric hindrance seems to be a limitation of the reaction, as amines carrying large substituents are not well converted. The same methodology can be applied to the coupling of secondary amines with 2-bromostyrene. Moreover, the reaction with substituted 2-bromopropenes allows regioselective synthesis of isomerizable terminal enamines without isomerization of the double bond. The best catalytic conditions for the cross-coupling of 1-bromostyrene with primary amines include again the use of the Pd°/BINAP/NaOtBu system. The reaction gives rise to the expected imines in very short times and with low catalyst loadings. A set of structurally diverse imines can be prepared by this methodology through variations in the structure of both coupling partners. However, 2-bromostyrene failed to give good results in this coupling reaction, probably due to product inhibition of the catalytic cycle. Competition experiments of vinyl versus aryl amination reveal that the reaction occurs preferentially on vinyl bromides.
Selectivity in the N- and/or C-Alkylation of Schiff Bases Catalyzed by Crown Ether
Akabori, Sadatoshi,Ohtomi, Michiko,Shimada, Kazuhide,Takemura, Ayami
, p. 1273 - 1274 (2007/10/02)
The reaction of anions derived from Schiff bases (N-(α-methylbenzylidene)aniline and N-cyclohexylideneaniline) with ethyl iodide or diethyl sulfate in aprotic solvents, in the presence of 18-crown-6, is found to give a high ratio of N/(N+C) or C/(N+C) alkylation when conducted in benzene or in dioxane.
Catalytic and Non-catalytic Addition of Aromatic Amines to Terminal Acetylenes in the Presence of Mercury(II) Chloride and Acetate
Barluenga, Jose,Aznar, Fernando,Liz, Ramon,Rodes, Rosa
, p. 2732 - 2737 (2007/10/02)
The addition of aromatic amines to terminal acetylenes in the presence of catalytic amounts of mercury(II) chloride gives imines, enamines, and 1,2,3,4-tetrahydroquinoline derivatives; mercury(II) acetate shows considerably less catalytic activity and may be used for the non-catalytic preparation of imines, enamines, N,N'-disubstituted acetamidines, and N,N-disubstituted acetamides.
