73500-16-0Relevant academic research and scientific papers
Regioselective reduction of 1h-1,2,3-triazole diesters
Butler, Christopher R.,Bendesky, Justin,Schoffstall, Allen Milton
, (2021/09/24)
Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding.
Azide-alkyne cycloadditions in a vortex fluidic device: Enhanced "on water" effects and catalysis in flow
Oksdath-Mansilla, Gabriela,Kucera, Renata L.,Chalker, Justin M.,Raston, Colin L.
supporting information, p. 659 - 662 (2021/01/29)
The Vortex Fluidic Device is a flow reactor that processes reactions in thin films. Running the metal-free azide-alkyne cycloaddition in this reactor revealed a dramatic enhancement of the "on water"effect. For the copper-catalyzed azide-alkyne cycloaddit
Visible-Light-Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron-Transfer Strategy
Wu, Zheng-Guang,Liao, Xiang-Ji,Yuan, Li,Wang, Yi,Zheng, You-Xuan,Zuo, Jing-Lin,Pan, Yi
supporting information, p. 5694 - 5700 (2020/04/24)
Click chemistry focuses on the development of highly selective reactions using simple precursors for the exquisite synthesis of molecules. Undisputedly, the CuI-catalyzed azide–alkyne cycloaddition (CuAAC) is one of the most valuable examples of click chemistry, but it suffers from some limitations as it requires additional reducing agents and ligands as well as cytotoxic copper. Here, we demonstrate a novel strategy for the azide–alkyne cycloaddition reaction that involves a photoredox electron-transfer radical mechanism instead of the traditional metal-catalyzed coordination process. This newly developed photocatalyzed azide–alkyne cycloaddition reaction can be performed under mild conditions at room temperature in the presence of air and visible light and shows good functional group tolerance, excellent atom economy, high yields of up to 99 %, and absolute regioselectivity, affording a variety of 1,4-disubstituted 1,2,3-triazole derivatives, including bioactive molecules and pharmaceuticals. The use of a recyclable photocatalyst, solar energy, and water as solvent makes this photocatalytic system sustainable and environmentally friendly. Moreover, the azide–alkyne cycloaddition reaction could be photocatalyzed in the presence of a metal-free catalyst with excellent regioselectivity, which represents an important development for click chemistry and should find versatile applications in organic synthesis, chemical biology, and materials science.
Water as a solvent for Ru-catalyzed click reaction: Highly efficient recyclable catalytic system for triazolocoumarins synthesis
Arafa, Wael Abdelgayed Ahmed,Nayl, Abd El-Aziz Ahmed
, (2019/08/21)
A new family of Ru (III) complexes has been synthesized, characterized and their catalytic performance has been tested for alkyne–azide cycloaddition (AAC) in water under ultrasonic irradiation conditions. These complexes are found to be effective heterog
An efficient and recyclable thiourea-supported copper(i) chloride catalyst for azide-alkyne cycloaddition reactions
Barman, Milan Kr.,Sinha, Ashish Kumar,Nembenna, Sharanappa
, p. 2534 - 2541 (2016/05/19)
A reaction between two equivalents of bulky thiourea, i.e., 1,3-bis(2,6-dimethylphenyl)thiourea (L) [L = (ArNH)2C = S; Ar = 2,6-Me2C6H3], and CuCl2 or CuCl in THF solvent afforded a bulky thiourea-sta
Metal-Free Intermolecular Azide-Alkyne Cycloaddition Promoted by Glycerol
Rodríguez-Rodríguez, Marta,Gras, Emmanuel,Pericàs, Miquel A.,G?mez, Montserrat
supporting information, p. 18706 - 18710 (2016/01/25)
Metal-free intermolecular Huisgen cycloadditions using nonactivated internal alkynes have been successfully performed in neat glycerol, both under thermal and microwave dielectric heating. In sharp contrast, no reaction occurs in other protic solvents, su
Copper malonamide complexes and their use in azide-alkyne cycloaddition reactions
Bent,Mahon,Webster
, p. 10253 - 10258 (2015/06/08)
We report a rare example of the malonamide functionality being used as a ligand in copper catalysis. We have ligated a homologous series of these O,O-chelating architectures to copper, investigated their structure and exploited them in azide-alkyne cycloa
Iridium-catalyzed intermolecular azide-alkyne cycloaddition of internal thioalkynes under mild conditions
Ding, Shengtao,Jia, Guochen,Sun, Jianwei
supporting information, p. 1877 - 1880 (2014/03/21)
An iridium-catalyzed azide-alkyne cycloaddition reaction (IrAAC) of electron-rich internal alkynes is described. It is the first efficient intermolecular AAC of internal thioalkynes. The reaction exhibits remarkable features, such as high efficiency and r
Transient protection of strained alkynes from click reaction via complexation with copper
Yoshida, Suguru,Hatakeyama, Yasutomo,Johmoto, Kohei,Uekusa, Hidehiro,Hosoya, Takamitsu
supporting information, p. 13590 - 13593 (2015/02/05)
A transient protection method of cyclooctynes from a click reaction with an azide through 1:1 complexation with a cationic copper(I) salt is reported. The application of the method to a cyclooctyne bearing a terminal alkyne enabled the selective copper-catalyzed click conjugation with an azide at the terminal alkyne moiety, which made cyclooctyne derivatives readily accessible.
An abnormal N-heterocyclic carbene-copper(I) complex in click chemistry
Sau, Samaresh Chandra,Roy, Sudipta Raha,Sen, Tamal K.,Mullangi, Dinesh,Mandal, Swadhin K.
, p. 2982 - 2991 (2014/03/21)
Herein we report the synthesis of a copper(I) chloro complex using an abnormal N-heterocyclic carbene (aNHC) salt, 1,3-bis(2,6-diisopropylphenyl)-2,4- diphenylimidazolium. The Cu(aNHC) complex efficiently catalyzed Huisgen 1,3-dipolar cycloaddition reacti
