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碳酸银介导的单金属富勒烯Y@C(9)-C与N-芳基苯甲脒的区域选择性自由基反应

Regioselective Radical Reaction of Monometallofullerene Y@C(9)-C With N-arylbenzamidine Mediated by Silver Carbonate.

作者信息

Li Jia, Yu Pengyuan, Lai Peng, Zou Jiajun, Liu Zhe, Yi Xiuguang, Wang Wei, Pan Changwang

机构信息

School of Chemistry and Chemical Engineering, Jinggangshan University, Ji'an, China.

State Key Laboratory of Materials Processing and Die & Mold Technology, School of Materials Science and Engineering, Huazhong University of Science and Technology, Wuhan, China.

出版信息

Front Chem. 2020 Oct 20;8:593602. doi: 10.3389/fchem.2020.593602. eCollection 2020.

DOI:10.3389/fchem.2020.593602
PMID:33195099
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7606928/
Abstract

A novel radical reaction of monometallofullerene Y@C(9)-C with N-arylbezamidine () is successfully conducted through catalysis with silver carbonate. The high-performance liquid chromatographic and mass spectrum results demonstrate that the reaction is highly regioselective to afford only one monoadduct () with an imidazoline group added on C cage, and computations through density functional theory reveal the addition group is attached to a specific [5, 6]-bond (C20-C76) near the Y atom. Furthermore, the analysis of prymidalization angle of the carbon atoms demonstrates the geometry of carbon cage is in favor of the regioselective formation of isomer (20, 76).

摘要

通过碳酸银催化，成功实现了单金属富勒烯Y@C(9)-C与N-芳基苯甲脒（）的新型自由基反应。高效液相色谱和质谱结果表明，该反应具有高度的区域选择性，仅生成一种在C笼上添加了咪唑啉基团的单加合物（），密度泛函理论计算表明，加成基团连接在Y原子附近的特定[5, 6]键（C20-C76）上。此外，对碳原子金字塔化角度的分析表明，碳笼的几何结构有利于异构体（20, 76）的区域选择性形成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b7a/7606928/e18dc2dc2046/fchem-08-593602-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b7a/7606928/a4d6b44a5b01/fchem-08-593602-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b7a/7606928/01752b3521d4/fchem-08-593602-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b7a/7606928/eb2787c9165a/fchem-08-593602-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b7a/7606928/4314dc0def27/fchem-08-593602-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b7a/7606928/e18dc2dc2046/fchem-08-593602-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b7a/7606928/a4d6b44a5b01/fchem-08-593602-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b7a/7606928/01752b3521d4/fchem-08-593602-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b7a/7606928/eb2787c9165a/fchem-08-593602-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b7a/7606928/4314dc0def27/fchem-08-593602-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b7a/7606928/e18dc2dc2046/fchem-08-593602-g0005.jpg

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本文引用的文献

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Structurally Precise Dichalcogenolate-Protected Copper and Silver Superatomic Nanoclusters and Their Alloys.结构精确的二硫属化物保护的铜和银超原子纳米团簇及其合金
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Isolation and Crystallographic Characterization of the Labile Isomer of Y@C82 Cocrystallized with Ni(OEP): Unprecedented Dimerization of Pristine Metallofullerenes.与 Ni(OEP)共晶化的 Y@C82 易变异构体的分离和晶体学表征：原始金属富勒烯的前所未有的二聚化。
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Silver(I)-mediated three-component annulation reaction of [60]fullerene, sulfonylhydrazones, and nitriles: leading to diverse disubstituted [60]fullerene-fused dihydropyrroles.银（I）介导的[60]富勒烯、磺酰腙和腈的三组分环化反应：生成多种二取代的[60]富勒烯稠合二氢吡咯。
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