123846-86-6Relevant articles and documents
An efficient and easily-accessible ligand for Cu(i)-catalyzed azide-alkyne cycloaddition bioconjugation
Guo, Yuan-Yang,Zhang, Bo,Wang, Luying,Huang, Shenlong,Wang, Shilei,You, Yanbo,Zhu, Gongming,Zhu, Anlian,Geng, Mingwei,Li, Lingjun
supporting information, p. 14401 - 14403 (2020/12/01)
A novel ligand (6) for copper-catalyzed azide-alkyne cycloaddition (CuAAC) in bioconjugation has been developed. Both in vitro and in vivo experiments indicate that 6 is more efficient and less cytotoxic than the canonical CuAAC ligands. Besides, 6 is easily accessible and can be prepared at gram scale. Our study reveals that 6 might be an ideal CuAAC ligand for bioconjugations.
Multi-component syntheses of diverse 5-fluoroalkyl-1,2,3-triazoles facilitated by air oxidation and copper catalysis
Zhu, Anlian,Xing, Xiaofang,Wang, Shilei,Yuan, Donghe,Zhu, Gongming,Geng, Mingwei,Guo, Yuanyang,Zhang, Guisheng,Li, Lingjun
supporting information, p. 3407 - 3412 (2019/06/24)
Air is an ideal oxidant due to its abundance, low cost and lack of toxic by-products. However, the catalytic aerobic oxidation reaction using air as an oxidant is still challenging due to its reduced activity and poor selectivity. In this study, a new class of glycinamide-type ligands was successfully synthesized and utilized for the aerobic oxidative reaction via in situ trapping of the formed triazolides with the nucleophilic fluoroalkyl reagents. By this designed oxidative procedure, various 5-fluoroalkyl-1,2,3-triazoles could be synthesized from available fluoroalkyl reagents, terminal alkynes and organic azides via one-pot reactions. Air was used as the sole oxidant; this significantly reduced the cost of this transformation, and the resulting operations and work-up procedures were significantly simplified. Alkyl azides and alkynes bearing various functional groups and natural structural motifs, and even aryl azides, which were ineffective in other reported methods, reacted efficiently under the current conditions. Different fluoroalkyl reagents, including trifluoromethyl trimethylsilane (CF3TMS), pentafluoroethyl trimethylsilane (C2F5TMS) and heptafluoropropyl trimethylsilane (C3F7TMS), could be used effectively for these reactions. The mechanistic study further indicates that the new N,O-ligand can stabilize the Cu(i) catalyst in a multiple binding mode and effectively promote the generation of oxidative coupling products; high efficiency together with a wider substrate scope has enlisted this copper-catalyzed aerobic coupling reaction among the most efficient methods for the preparation of 5-fluoroalkyl 1,2,3-triazoles.
Synthesis method of new ligand for efficient catalysis of CuAAC reaction
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Paragraph 0013; 0014; 0015, (2018/03/28)
Belonging to the technical field of synthesis of functional structural molecules, the invention discloses a synthesis method of a new ligand for efficient catalysis of CuAAC reaction. The key point ofthe technical scheme adopted by the invention lies in that: the synthesis method of the new ligand for efficient catalysis of CuAAC reaction includes: firstly synthesizing glycine methyl ester diyne,then taking glycine methyl ester diyne, an azido compound, K2CO3 and copper iodide as the raw materials, using acetonitrile and water as the solvent, carrying out stirring reaction at room temperature, and performing post-treatment at the end of reaction, thus obtaining the new ligand glycine methyl ester 1, 2, 3-ditriazole ring opening compound. The invention provides a variety of novel, efficient and easily available ligand catalysts for click reaction, as a ligand, the compound synthesized by the method provided by the invention has obvious effect of accelerating reaction and has a very practical application.
Medium Rings Bearing Bitriazolyls: Easily Accessible Structures with Superior Performance as Cu Catalyst Ligands
Li, Lingjun,Huang, Shenlong,Shang, Tongpeng,Zhang, Bo,Guo, Yuanyang,Zhu, Gongming,Zhou, Demin,Zhang, Guisheng,Zhu, Anlian,Zhang, Lihe
, p. 13166 - 13177 (2018/11/02)
Benefiting from their unique properties, the development of structurally novel and easily accessible medium rings is of significant interest in the pharmaceutical industry and academic research. However, synthetic access to medium-ring scaffolds is very d
Preparation method of 1,2,3-bis-triazole ligands and application of 1,2,3-bis-triazole ligands in CuAAC reaction
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Paragraph 0006; 0008; 0015, (2018/02/04)
The invention discloses a preparation method of 1,2,3-bis-triazole ligands and an application of the 1,2,3-bis-triazole ligands in a CuAAC reaction. With cheap and easily available glycine methyl ester hydrochloride as a base raw material, and through derivation and conversion of functional groups, a diyne compound with glycine as a structure is obtained; then under a condition of room temperature and with organic azide as a raw material and copper iodide as a catalyst, 1,2,3-bis-triazole seven-membered-ring compounds are synthesized; and with the bis-triazole compounds and derivatives thereof as substrates, a series of methods for synthesis of the 1,2,3-bis-triazole derivatives are developed. A variety of novel, highly efficient, simple and easily available ligand catalysts are provided for a click reaction, and the 1,2,3-bis-triazole ligands have obvious effect on accelerating the reaction when used as the ligands and have quite practical application.
