6628-07-5Relevant academic research and scientific papers
A soluble and reusable colorimetric sensor based on the covalent attachment of a triarylpentenedione to poly(ethylene glycol)
Alvaro, Mercedes,Aprile, Carmela,Garcia, Hermenegildo,Peris, Encarna
, p. 3045 - 3051 (2005)
3-(4-Aminophenyl)-1,5-diphenylpent-2-ene-1,5-dione (PDO) is a colorimetric sensor of Lewis acid cations that has been covalently attached to a poly(ethylene glycol) (PEG) scaffold. The resulting PDO-PEG is soluble in water and other organic solvents and a
1,3,5-Triaryl-2-penten-1,5-dione anchored to insoluble supports as heterogeneous chromogenic chemosensor
Alvaro, Mercedes,Aprile, Carmela,Corma, Avelino,Fornes, Vicente,Garcia, Hermenegildo,Peris, Encarna
, p. 8257 - 8263 (2004)
N-Allyl substituted 1,5-diphenyl-3-(4-N-methylaminophenyl)-2-penten-1,5- dione (1a) has been immobilized on a polystyrene backbone, on the surface of mercaptopropyl-functionalized silica or inside the cavities of zeolite NaY. These solids either in suspen
Copper-Catalyzed Allylation of Amines with Cyclopropyldiphenylsulfonium Trifluoromethanesulfonate
Ma, Yu,Tian, Ze-Yu,Zhang, Cheng-Pan,Zheng, Shuang-Yang
supporting information, (2022/03/15)
Cyclopropyldiphenylsulfonium salt, a famous ylide precursor previously extensively employed in the preparation of cyclic compounds, has been successfully utilized as an efficient allylation reagent in this work. The copper-catalyzed reactions of cyclopropyldiphenylsulfonium trifluoromethanesulfonate with amines in the presence of an appropriate ligand provided the N-allylated products in good yields. Aliphatic/ aromatic amines and primary/secondary amines were all converted under mild reaction conditions. This protocol was also applicable to N-functionalization of drug molecules, supplying the corresponding N-allylated compounds in satisfactory yields. The reaction, which showed good functional group tolerance with a wide range of substrates and excellent chemoselectivity, offers an interesting method for the synthesis of N-allyl amines.
Aerobic Allylic Amination Catalyzed by a Pd(OAc)2/P(OPh)3System with Low Catalyst Loading
Yurino, Taiga,Saito, Sunaho,Ichihashi, Mizuki,Ohkuma, Takeshi
supporting information, p. 2864 - 2872 (2022/02/14)
A Pd(OAc)2/P(OPh)3 combination catalyzed Tsuji-Trost-Type allylic amination under aerobic conditions. Both aromatic and aliphatic secondary amines were transformed into the corresponding allylic amines with a tiny amount of the catalyst system (typically 0.02 mol % Pd), only when allylic phosphates were employed as electrophiles. Other typical electrophiles, such as allylic acetate and carbonate, were marginally reactive. A Pd(0) complex, Pd[P(OPh)3]3, formed in situ was suggested as an active species by mechanistic experiments.
Nickel-Catalyzed Hydrosilylation of Terminal Alkenes with Primary Silanes via Electrophilic Silicon-Hydrogen Bond Activation
Wu, Xiaoyu,Ding, Guangni,Lu, Wenkui,Yang, Liqun,Wang, Jingyang,Zhang, Yuxuan,Xie, Xiaomin,Zhang, Zhaoguo
supporting information, p. 1434 - 1439 (2021/02/16)
We report a simple and effective nickel-based catalytic system, NiCl2·6H2O/tBuOK, for the electrophilically activated hydrosilylation of terminal alkenes with primary silanes. This protocol provides excellent performance under mild reaction conditions: ex
Visible light-induced N-methyl activation of unsymmetric tertiary amines
Perumal, Gopi,Kandasamy, Mohanraj,Ganesan, Balaji,Govindan, Karthick,Sathya, Harsha,Hung, Min-Yuan,Chandru Senadi, Gopal,Wu, Ya-Ching,Lin, Wei-Yu
supporting information, (2021/01/09)
In the presence of methylene group, selective N-methyl activation of tertiary amines has been accomplished with the aid of visible light using organic photocatalyst under air. This protocol explores numerous aliphatic and aromatic substituted tetra-hydroquinoline analogues from various tertiary amines and maleimides. Furthermore, this approach was applied to activate the methyl group of N-methyl carbazole to generate the biologically active molecule.
Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes
Cho, Seoyoung,McLaren, E. J.,Wang, Qiu
supporting information, p. 26332 - 26336 (2021/11/10)
Difunctionalization of strained cyclic alkynes presents a powerful strategy to build richly functionalized cyclic alkenes in an expedient fashion. Herein we disclose an efficient and flexible approach to achieve carbohalogenation, dicarbofunctionalization, aminohalogenation and aminocarbonation of readily available cyclohexenyl triflates. We have demonstrated the novel use of zincate base/nucleophile system for effective formation of key cyclohexyne intermediates and selective addition of various carbon and nitrogen nucleophiles. Importantly, leveraging the resulting organozincates enables the incorporation of a broad range of electrophilic partners to deliver structurally diverse cyclohexene motifs. The importance and utility of this method is also exemplified by the modularity of this approach and the ease in which even highly complex polycyclic scaffolds can be accessed in one step.
Dirhodium(II)/Xantphos-Catalyzed Relay Carbene Insertion and Allylic Alkylation Process: Reaction Development and Mechanistic Insights
Liang, Xinyi,Lu, Bin,Peng, Qian,Wang, Xiaoming,Wang, Zijian,Zhang, Jinyu
supporting information, p. 11799 - 11810 (2021/08/16)
Although dirhodium-catalyzed multicomponent reactions of diazo compounds, nucleophiles and electrophiles have achieved great advance in organic synthesis, the introduction of allylic moiety as the third component via allylic metal intermediate remains a formidable challenge in this area. Herein, an attractive three-component reaction of readily accessible amines, diazo compounds, and allylic compounds enabled by a novel dirhodium(II)/Xantphos catalysis is disclosed, affording various architecturally complex and functionally diverse α-quaternary α-amino acid derivatives in good yields with high atom and step economy. Mechanistic studies indicate that the transformation is achieved through a relay dirhodium(II)-catalyzed carbene insertion and allylic alkylation process, in which the catalytic properties of dirhodium are effectively modified by the coordination with Xantphos, leading to good activity in the catalytic allylic alkylation process.
Visible-Light-Induced C(sp2)-C(sp3) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl- N-methylanilines under Mild Conditions
Zhang, Hong-Yu,Chen, Jianjun,Lu, Cong-Cong,Han, Ya-Ping,Zhang, Yuecheng,Zhao, Jiquan
, p. 11723 - 11735 (2021/09/02)
Disclosed herein is a cross-dehydrogenative-coupling reaction of N-heterocycles including 1,2,4-triazine-3,5(2H, 4H)-diones and quinoxaline-2(1H)-ones with N-methylanilines to form C(sp2)-C(sp3) under visible-light illumination and ambient air at room temperature. In this process, easily available Ru(bpy)3Cl2·6H2O serves as the catalyst, and air acts as the green oxidant. This method features high atom economy, environmental friendliness, and convenient operation and provides an efficient and practical access to aminomethyl-substituted N-heterocycles with extensive functional group compatibility in 40-86% yields.
Photo-induced dealdehyding method
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Paragraph 0048-0053; 0174-0179, (2020/06/16)
The invention provides a photo-induced dealdehyding method, and belongs to the technical field of organic synthesis. The photo-induced dealdehyding method comprises the following steps that a mixtureof a compound shown in the formula I and a solvent are reacted under an inert gas atmosphere and visible light irradiation, a dealdehyding product is obtained, and no photocatalyst is used in the whole process; wherein the structural formula of the formula I shown in the specification, R is a functional group and is selected from hydrogen, methyl, methoxyl, cyano, chlorine, bromine or fluorine. According to the photo-induced dealdehyding method, in the inert gas atmosphere, the compound shown in the formula (I) can be excited to generate carbon-oxygen bond homogeneous cracking through visiblelight irradiation, then free radical migration and double bond displacement are conducted, finally carbon monoxide is removed, aldehyde group removal is completed, no photocatalyst is needed in the whole process, operation is easy and convenient, and conditions are mild.
