TEMPO-Mediated Synthesis of Tetrahydropyridinofullerenes: Reaction of [60]Fullerene with α-Methyl-Substituted Arylmethanamines and Aldehydes in the Presence of 4-Dimethylaminopyridine

被引：24

作者：

Peng, Jie ^{[1
,2
]}

Huang, Gang ^{[1
,2
]}

Wang, Hui-Juan ^{[3
]}

Li, Fa-Bao ^{[1
,2
]}

Huang, Cheng ^{[1
,2
]}

Xiang, Jun-Jun ^{[1
,2
]}

Huang, Yongshun ^{[1
,2
]}

Liu, Li ^{[1
,2
]}

Liu, Chao-Yang ^{[3
]}

Asiri, Abdullah M. ^{[4
]}

Alarmry, Khalid A. ^{[4
]}

机构：

[1] Hubei Univ, Hubei Collaborat Innovat Ctr Adv Organ Chem Mat, Key Lab Synth & Applicat Organ Funct Mol,Minist, Key Lab Green Preparat & Applicat Funct Mat, Wuhan 430062, Hubei, Peoples R China

[2] Hubei Univ, Sch Chem & Chem Engn, Wuhan 430062, Hubei, Peoples R China

[3] Chinese Acad Sci, Wuhan Ctr Magnet Resonance, Wuhan Inst Phys & Math, State Key Lab Magnet Resonance & Atom & Mol Phys, Wuhan 430071, Hubei, Peoples R China

[4] King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 01期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTION; SELECTIVE FORMATION; AROMATIC-ALDEHYDES; MOLECULAR-OXYGEN; FULLERENE; C-60; DERIVATIVES; CHEMISTRY; AMINES; BUCKMINSTERFULLERENE;

D O I：

10.1021/acs.joc.7b02378

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of scarce tetrahydropyridinofullerenes were synthesized by the metal-free-mediated reaction of [60]fullerene with cheap and easily available alpha-methyl-substituted arylmethanamines and aldehydes in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and 4-dimethylaminopyridine (DMAP) in moderate to good yields comparable to the previously reported data for most monoadducts. The in situ generation of azadienes played a crucial role in the successful synthesis of tetrahydropyridinofullerenes. A plausible reaction mechanism was proposed to elucidate the reaction process.

引用

页码：85 / 95

页数：11

共 21 条

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[2] Metal-free-mediated synthesis of fulleropyrrolines by the reaction of [60]fullerene with β-substituted ethylamines
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