Metal-Free Synthesis of N-Alkyl-2,5-Unsubstituted/Monosubstituted Fulleropyrrolidines: Reaction of [60]Fullerene with Paraformaldehyde and Amines

doi:10.1021/acs.joc.9b00083

	Metal-Free Synthesis of N-Alkyl-2,5-Unsubstituted/Monosubstituted Fulleropyrrolidines: Reaction of [60]Fullerene with Paraformaldehyde and Amines
	Alamry, Khalid A.1; Asiri, Abdullah M.1; Liu, Chao-Yang 2; Liu, Li 3,4; Sun, Liang 3,4; Li, Fa-Bao 3,4; Wang, Hui-Juan 2; Zhang, Duo 3,4; Li, Yun-Fei 3,4
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2019-03-01
卷号	84 期号:5 页码:2922-2932
ISSN号	0022-3263
DOI	10.1021/acs.joc.9b00083
英文摘要	A series of scarce N-alkyl-2,5-unsubstituted/mono-substituted fulleropyrrolidines were synthesized in moderate to excellent yields by the simple one-step thermal reaction of [60]fullerene with primary/secondary amines in the presence of paraformaldehyde without the addition of valuable metal salts. Intriguingly, the reaction with primary amines unexpectedly afforded N-alkyl-2,5-unsubstituted fulleropyrrolidines instead of the anticipated 2,5-monosubstituted fulleropyrrolidines. A plausible reaction pathway is proposed to elucidate the above-mentioned reaction process based on the experimental results.
资助项目	National Natural Science Foundation of China[21102041] ; National Natural Science Foundation of China[21671061] ; National Natural Science Foundation of China[11575287] ; Scientific Research Foundation of Education Commission of Hubei Province[D20161007] ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province[201710512044] ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province[201810512046] ; Open Project of State Key Laboratory of Silicate Materials for Architectures (Wuhan University of Technology)[SYSJJ2019-10]
WOS关键词	ELECTRON-TRANSFER ; AROMATIC-ALDEHYDES ; ADDITION-REACTIONS ; MEDIATED SYNTHESIS ; CHIRAL FULLERENES ; AZOMETHINE YLIDES ; C-60 ; FUNCTIONALIZATION ; CYCLOADDITION ; CHEMISTRY
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000460491600049
资助机构	National Natural Science Foundation of China ; National Natural Science Foundation of China ; Scientific Research Foundation of Education Commission of Hubei Province ; Scientific Research Foundation of Education Commission of Hubei Province ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province ; Open Project of State Key Laboratory of Silicate Materials for Architectures (Wuhan University of Technology) ; Open Project of State Key Laboratory of Silicate Materials for Architectures (Wuhan University of Technology) ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Scientific Research Foundation of Education Commission of Hubei Province ; Scientific Research Foundation of Education Commission of Hubei Province ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province ; Open Project of State Key Laboratory of Silicate Materials for Architectures (Wuhan University of Technology) ; Open Project of State Key Laboratory of Silicate Materials for Architectures (Wuhan University of Technology) ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Scientific Research Foundation of Education Commission of Hubei Province ; Scientific Research Foundation of Education Commission of Hubei Province ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province ; Open Project of State Key Laboratory of Silicate Materials for Architectures (Wuhan University of Technology) ; Open Project of State Key Laboratory of Silicate Materials for Architectures (Wuhan University of Technology) ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Scientific Research Foundation of Education Commission of Hubei Province ; Scientific Research Foundation of Education Commission of Hubei Province ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province ; Innovation and Entrepreneurship Training Program for Undergraduates of Hubei Province ; Open Project of State Key Laboratory of Silicate Materials for Architectures (Wuhan University of Technology) ; Open Project of State Key Laboratory of Silicate Materials for Architectures (Wuhan University of Technology)
内容类型	期刊论文
源URL	[http://ir.wipm.ac.cn/handle/112942/14133]
专题	中国科学院武汉物理与数学研究所
通讯作者	Liu, Chao-Yang; Li, Fa-Bao
作者单位	1.King Abdulaziz Univ, Dept Chem, Fac Sci, Jeddah 21589, Saudi Arabia 2.Chinese Acad Sci, Wuhan Inst Phys & Math, Wuhan Ctr Magnet Resonance, State Key Lab Magnet Resonance & Atom & Mol Phys, Wuhan 430071, Hubei, Peoples R China 3.Hubei Univ, Sch Chem & Chem Engn, Wuhan 430062, Hubei, Peoples R China 4.Hubei Univ, Hubei Collaborat Innovat Ctr Adv Organ Chem Mat, Key Lab Green Preparat & Applicat Funct Mat, Key Lab Synth & Applicat Organ Funct Mol,Minist E, Wuhan 430062, Hubei, Peoples R China
推荐引用方式 GB/T 7714	Alamry, Khalid A.,Asiri, Abdullah M.,Liu, Chao-Yang,et al. Metal-Free Synthesis of N-Alkyl-2,5-Unsubstituted/Monosubstituted Fulleropyrrolidines: Reaction of [60]Fullerene with Paraformaldehyde and Amines[J]. JOURNAL OF ORGANIC CHEMISTRY,2019,84(5):2922-2932.
APA	Alamry, Khalid A..,Asiri, Abdullah M..,Liu, Chao-Yang.,Liu, Li.,Sun, Liang.,...&Li, Yun-Fei.(2019).Metal-Free Synthesis of N-Alkyl-2,5-Unsubstituted/Monosubstituted Fulleropyrrolidines: Reaction of [60]Fullerene with Paraformaldehyde and Amines.JOURNAL OF ORGANIC CHEMISTRY,84(5),2922-2932.
MLA	Alamry, Khalid A.,et al."Metal-Free Synthesis of N-Alkyl-2,5-Unsubstituted/Monosubstituted Fulleropyrrolidines: Reaction of [60]Fullerene with Paraformaldehyde and Amines".JOURNAL OF ORGANIC CHEMISTRY 84.5(2019):2922-2932.