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Facile access to amino-substituted cyclopentafullerenes: novel reaction of [60]fullerene with beta-substituted propionaldehydes and secondary amines in the absence/presence of magnesium perchlorate

文献类型：期刊论文

作者Li, Yun-Fei1,2; Wang, Kun1,2; Wang, Hui-Juan3; Li, Fa-Bao1,2; Sun, Rui1,2; Li, Jia-Xing4; Liu, Li1,2; Liu, Chao-Yang3; Asiri, Abdullah M.5
刊名ORGANIC & BIOMOLECULAR CHEMISTRY
出版日期2020-09-21
卷号18
ISSN号1477-0520
DOI10.1039/d0ob00008f
通讯作者Li, Fa-Bao(lfb0615@hubu.edu.cn) ; Li, Jia-Xing(lijx@ipp.ac.cn) ; Liu, Chao-Yang(chyliu@wipm.ac.cn)
英文摘要A series of scarce amino-substituted cyclopentafullerenes instead of the expectedN-alkyl-2,5-disubstituted fulleropyrrolidines were synthesized in moderate to excellent yieldsviathe simple one-step reaction of [60]fullerene with cheap and easily available beta-substituted propionaldehydes and secondary amines in the absence/presence of magnesium perchlorate. Thein situgeneration of allylic amines from beta-substituted propionaldehydes and secondary amines played a crucial role in the successful preparation of amino-substituted cyclopentafullerenes without additional carbons. With the addition of magnesium perchlorate, secondary amines containing ethyl group(s) could produce novel amino-substituted cyclopentafullerenes with two additional carbons. All the obtained cyclopentafullerenes displayed high stereoselectivity withcisisomers as the exclusive or major products. Plausible reaction mechanisms are proposed to elucidate the above-mentioned reaction process.
WOS关键词MEDIATED SYNTHESIS ; AROMATIC-ALDEHYDES ; ELECTRON-TRANSFER ; FULLERENE ; FULLEROPYRROLIDINES ; DERIVATIVES ; CHEMISTRY ; FUNCTIONALIZATION ; ARYLMETHANAMINES ; CYCLOADDITION
资助项目National Natural Science Foundation of China[21102041] ; National Natural Science Foundation of China[11575287] ; National Natural Science Foundation of China[21671061] ; Open Project of State Key Laboratory of Silicate Materials for Architectures (Wuhan University of Technology)[SYSJJ2019-10] ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province[201810512046] ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province[S201910512013] ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province[S202010512053]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000571281400011
出版者ROYAL SOC CHEMISTRY
资助机构National Natural Science Foundation of China ; Open Project of State Key Laboratory of Silicate Materials for Architectures (Wuhan University of Technology) ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province
源URL[http://ir.hfcas.ac.cn:8080/handle/334002/104272]  
专题中国科学院合肥物质科学研究院
通讯作者Li, Fa-Bao; Li, Jia-Xing; Liu, Chao-Yang
作者单位1.Hubei Univ, Minist Educ, Key Lab Synth & Applicat Organ Funct Mol, Hubei Key Lab Polymer Mat, Wuhan 430062, Peoples R China
2.Hubei Univ, Sch Chem & Chem Engn, Wuhan 430062, Peoples R China
3.Chinese Acad Sci, Wuhan Inst Phys & Math, Wuhan Ctr Magnet Resonance, State Key Lab Magnet Resonance & Atom & Mol Phys, Wuhan 430071, Peoples R China
4.Chinese Acad Sci, Inst Plasma Phys, Key Lab Novel Thin Film Solar Cells, POB 1126, Hefei 230031, Peoples R China
5.King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia
推荐引用方式
GB/T 7714		 Li, Yun-Fei,Wang, Kun,Wang, Hui-Juan,et al. Facile access to amino-substituted cyclopentafullerenes: novel reaction of [60]fullerene with beta-substituted propionaldehydes and secondary amines in the absence/presence of magnesium perchlorate[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2020,18.
APA Li, Yun-Fei.,Wang, Kun.,Wang, Hui-Juan.,Li, Fa-Bao.,Sun, Rui.,...&Asiri, Abdullah M..(2020).Facile access to amino-substituted cyclopentafullerenes: novel reaction of [60]fullerene with beta-substituted propionaldehydes and secondary amines in the absence/presence of magnesium perchlorate.ORGANIC & BIOMOLECULAR CHEMISTRY,18.
MLA Li, Yun-Fei,et al."Facile access to amino-substituted cyclopentafullerenes: novel reaction of [60]fullerene with beta-substituted propionaldehydes and secondary amines in the absence/presence of magnesium perchlorate".ORGANIC & BIOMOLECULAR CHEMISTRY 18(2020).

入库方式： OAI收割

来源：合肥物质科学研究院

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