860002-66-0Relevant academic research and scientific papers
Copper (I)-mediated synthesis of trisubstituted 1,2,3-triazoles
Kuijpers, Brian H. M.,Dijkmans, Guido C. T.,Groothuys, Stan,Quaedflieg, Peter J. L. M.,Blaauw, Richard H.,Van Delft, Floris L.,Rutjes, Floris P. J. T.
, p. 3059 - 3062 (2005)
A copper-catalysed coupling of bromo-alkynes and organic azides is described. This coupling results in the formation of bromo-containing trisubstituted 1,2,3-triazole derivatives in high yield and a regioselective manner. Georg Thieme Verlag Stuttgart.
Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source
Yano De Albuquerque, Danilo,Teixeira, Wystan K. O.,Sacramento, Manoela Do,Alves, Diego,Santi, Claudio,Schwab, Ricardo S.
supporting information, p. 595 - 605 (2022/01/12)
A new catalytic protocol for the synthesis of selenoesters from aryl iodides and diaryl diselenides has been developed, where formic acid was employed as an efficient, low-cost, and safe substitute for toxic and gaseous CO. This protocol presents a high functional group tolerance, providing access to a large family of selenoesters in high yields (up to 97%) while operating under mild reaction conditions, and avoids the use of selenol which is difficult to manipulate, easily oxidizes, and has a bad odor. Additionally, this method can be efficiently extended to the synthesis of thioesters with moderate-to-excellent yields, by employing for the first time diorganyl disulfides as precursors.
Predicting the catalytic activity of azolium-based halogen bond donors: an experimentally-verified theoretical study
Bolotin, Dmitrii S.,Il'in, Mikhail V.,Novikov, Alexander S.,Suslonov, Vitalii V.,Sysoeva, Alexandra A.
supporting information, p. 7611 - 7620 (2021/09/22)
This report demonstrates the successful application of electrostatic surface potential distribution analysis for evaluating the relative catalytic activity of a series of azolium-based halogen bond donors. A strong correlation (R2> 0.97) was observed between the positive electrostatic potential of the σ-hole on the halogen atom and the Gibbs free energy of activation of the model reactions (i.e., halogen abstraction and carbonyl activation). The predictive ability of the applied approach was confirmed experimentally. It was also determined that the catalytic activity of azolium-based halogen bond donors was generally governed by the structure of the azolium cycle, whereas the substituents on the heterocycle had a limited impact on the activity. Ultimately, this study highlighted four of the most promising azolium halogen bond donors, which are expected to exhibit high catalytic activity.
Efficient copper-catalyzed tandem oxidative iodination and alkyne-azide cycloaddition in the presence of glycine-type ligands
Yuan, Donghe,Wang, Shilei,Zhu, Gongming,Zhu, Anlian,Li, Lingjun
, (2021/01/28)
Tandem oxidative iodination and alkyne-azide cycloaddition reaction has provided one of the most widely used methods for preparation of 5-iodo-1,2,3-triazoles. However, stoichiometric copper salts are involved in this type of reaction in order to enhance
Dinuclear Cu(I) Halides with Terphenyl Phosphines: Synthesis, Photophysical Studies, and Catalytic Applications in CuAAC Reactions
Beltrán, álvaro,Gata, Inmaculada,Maya, Celia,Avó, Jo?o,Lima, Jo?o Carlos,Laia, César A. T.,Peloso, Riccardo,Outis, Mani,Nicasio, M. Carmen
supporting information, p. 10894 - 10906 (2020/08/12)
Several dinuclear terphenyl phosphine copper(I) halide complexes of composition [CuX(PR2Ar′)]2 (X = Cl, Br, I; R = hydrocarbyl, Ar′ = 2,6-diarylterphenyl radical), 1-5, have been isolated from the reaction of CuX with 1 equiv of the phosphine ligand. Most
Copper(i) complexes bearing mesoionic carbene ligands: Influencing the activity in catalytic halo-click reactions
Beerhues, Julia,Etzold, Oliver,Sarkar, Biprajit,Suntrup, Lisa
, p. 15504 - 15510 (2020/11/18)
Metal complexes of mesoionic carbene (MIC) ligands are known to catalyze a variety of chemical transformations. In this contribution, we report on the synthesis of a dicationic dicopper(i) complex containing a di-MIC ligand. Two routes are presented for the synthesis of the dicopper complex: Ag-mediated transmetalation and direct deprotonation. For the Ag-mediated transmetalation route, the detection and isolation of several Ag-containing intermediates that are relevant for the final formation of the aforementioned dicopper complex are reported. We then investigate a series of copper(i) complexes based on MIC ligands as precatalysts for the azide halo-alkyne (Click) cycloaddition reaction. In a comparative study, three different halide-containing (I, Br, Cl) substrates have been investigated with different catalysts to survey the behaviour for mono/di-copper-MIC complexes as well as neutral, mono- and di-cationic complexes. The cationic complexes proved to have superior activities compared to the neutral species. These are the first reports on the use of Cu-MIC complexes as precatalysts for the halo-Click reaction.
Design, synthesis and comparative analysis of triphenyl-1,2,3-triazoles as anti-proliferative agents
Dheer, Divya,Behera, Chittaranjan,Singh, Davinder,Abdullaha, Mohd,Chashoo, Gousia,Bharate, Sandip B.,Gupta, Prem N.,Shankar, Ravi
, (2020/09/17)
Herein, a series of triaryl-1,2,3-triazoles, in order to check cytotoxicity on breast cancer cell lines have been synthesized with pendent benzyl ring to mimic the phenolic A ring of Tamoxifene. The biological results indicated that most of the compounds
Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,2,3-Triazole-5-carboxamides Using Dimethyl Carbonate as Sustainable Solvent
de Albuquerque, Danilo Yano,de Moraes, Juliana R.,Schwab, Ricardo S.
supporting information, p. 6673 - 6681 (2019/11/02)
A simple and direct palladium-catalyzed aminocarbonylation of 5-iodo-1,2,3-triazoles backbone for the incorporation of an amide functional group is presented. The approach is based on the palladium catalyzed carbonylative coupling reaction of iodo-triazole with different amines employing formic acid and sulfuric acid as CO source (Morgan's reaction) to provide the 1,2,3-triazole-5-carboxamides in good to excellent yields. The important features of this methodology include short reaction time, high yields, the use of dimethyl carbonate as a sustainable solvent, and the use of efficient alternative source of carbon monoxide, avoiding pressurized cylinder. The methodology described herein for the synthesis of 1,4,5-trisubstituted 1,2,3-triazole-5-carboxamides, can offers an alternative path for functionalization of other heterocycles.
Novel synthesis of 5-iodo-1,2,3-triazoles using an aqueous iodination system under air
Li, Lingjun,Xing, Xiaofang,Zhang, Chi,Zhu, Anlian,Fan, Xincui,Chen, Changpo,Zhang, Guisheng
supporting information, p. 3563 - 3566 (2018/08/31)
A novel aqueous iodination system was developed for the synthesis of 5-iodo-1,2,3-triazoles under air. This reaction system has high efficiency and excellent chemo-selectivity with wide functional group tolerance. In addition, this method can be utilized
Regioselective Approach to 5-Carboxy-1,2,3-triazoles Based on Palladium-Catalyzed Carbonylation
Kotovshchikov, Yury N.,Latyshev, Gennadij V.,Beletskaya, Irina P.,Lukashev, Nikolay V.
supporting information, p. 1926 - 1934 (2018/02/09)
A regioselective two-step approach to 5-carboxy-1,2,3-triazoles based on palladium-catalyzed carbonylation has been developed. The protocol utilizes readily available 5-iodotriazoles as starting materials. The obtained products were used in the syntheses
