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

doi:10.1039/d0ob00008f

HFCAS OpenIR

	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
	Li, Yun-Fei 1,2; Wang, Kun1,2 ; Wang, Hui-Juan 3; Li, Fa-Bao 1,2; Sun, Rui 1,2; Li, Jia-Xing4 ; Liu, Li 1,2; Liu, Chao-Yang 3; Asiri, Abdullah M.5
	2020-09-21
发表期刊	ORGANIC & BIOMOLECULAR CHEMISTRY
ISSN	1477-0520
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)
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.
DOI	10.1039/d0ob00008f
关键词[WOS]	MEDIATED SYNTHESIS ; AROMATIC-ALDEHYDES ; ELECTRON-TRANSFER ; FULLERENE ; FULLEROPYRROLIDINES ; DERIVATIVES ; CHEMISTRY ; FUNCTIONALIZATION ; ARYLMETHANAMINES ; CYCLOADDITION
收录类别	SCI
语种	英语
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]
项目资助者	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
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
WOS记录号	WOS:000571281400011
出版者	ROYAL SOC CHEMISTRY
引用统计	被引频次：4[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.hfcas.ac.cn:8080/handle/334002/104273
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
通讯作者单位	中科院等离子体物理研究所
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).