Synthesis of spiroindoline derivatives and biphenyl compounds in green solvent via a "capture-release" mechanism using modified polyacrylonitrile fiber as a catalyst

被引:4
作者
Li, Xiaoting [1 ]
Zhang, Yanfei [1 ]
Liu, Jinxin [1 ]
Cao, Jian [2 ]
Ma, Ning [1 ]
Tao, Minli [1 ,3 ]
Zhang, Wenqin [1 ]
机构
[1] Tianjin Univ, Sch Sci, Dept Chem, 135 Yaguan Rd,Haihe Educ Pk, Tianjin 300072, Peoples R China
[2] Langfang Normal Univ, Dept Chem & Mat Sci, Langfang 065000, Hebei, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R China
基金
中国国家自然科学基金;
关键词
Polyacrylonitrile fiber; Tertiary phosphine; Pd; Spiroindoline derivatives; Suzuki coupling; EFFICIENT SYNTHESIS; COUPLING REACTIONS; HIGHLY EFFICIENT; GRUBBS CATALYSTS; PALLADIUM; COMPLEXES; MICROENVIRONMENT; SPIROOXINDOLES; NANOPARTICLES; NANOCATALYST;
D O I
10.1016/j.cej.2024.153906
中图分类号
X [环境科学、安全科学];
学科分类号
08 ; 0830 ;
摘要
Green synthesis of critical bioactive molecules and fine chemicals is attracting increasing interest. This study investigates the use of two distinct functionalized polyacrylonitrile (PAN) fibers (PANEDBPF and PANEDBP-Pd effective catalysts in a green solvent comprising ethanol and water. Firstly, a PAN fiber was modified using 2(diphenylphosphino) ethylamine, a strongly nucleophilic phosphine compound, to obtain PANEDBPF. Spiroindoline derivatives were obtained in 98 % yields when the reaction was conducted using 5 mol% of PANEDBPF as the catalyst at 70 degrees C for 30 min. Next, we loaded PdNPs onto PANEDBPF to obtain PANEDBP-Pd Suzuki coupling reaction was conducted at room temperature (25 degrees C) using 0.5 mol% of PANEDBP-Pd 0 F, the products were obtained in an extremely high yield of 99 %. Additionally, the unique enrichment of the substrate by the functionalized fibers during the reaction and the subsequent release of the product from the microenvironment conform to the "capture-release" reaction mode of catalysis. Both PANEDBPF and PANEDBP-Pd demonstrated good gram-scale amplification, repeatability, catalytic activity, and stability. Hence, they are highly promising candidates for green chemistry applications.
引用
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页数:12
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