The Cu(II)-catalyzed -heteroannulation reaction of [60]fullerene (C) with aryl sulfonamides and paraformaldehyde has been disclosed for the synthesis of diverse C-fused imidazolidines, of which one or both of the ArSO moieties could be removed selectively. Further transformations into the unexpected bicyclic 1,2,3,4-adduct and C-fused imidazolidinium iodide salt have also been demonstrated. A plausible reaction mechanism is proposed on the basis of control experiments. C-fused imidazolidinium iodide has been employed as an additive in the PCBM layer of inverted planar perovskite solar cells to increase power conversion efficiency.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.5c00518 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Copper-Catalyzed -Heteroannulation of [60]Fullerene with Aryl Sulfonamides and Paraformaldehyde: Synthesis and Functionalization of [60]Fullerene-Fused Imidazolidines.
Org Lett
March 2025
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, and School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241002, People's Republic of China.
The Cu(II)-catalyzed -heteroannulation reaction of [60]fullerene (C) with aryl sulfonamides and paraformaldehyde has been disclosed for the synthesis of diverse C-fused imidazolidines, of which one or both of the ArSO moieties could be removed selectively. Further transformations into the unexpected bicyclic 1,2,3,4-adduct and C-fused imidazolidinium iodide salt have also been demonstrated. A plausible reaction mechanism is proposed on the basis of control experiments.
View Article and Find Full Text PDFReaction mechanism with indano[60]fullerene bromide for evaporable fullerene derivatives.
Chem Commun (Camb)
January 2025
Department of Chemical Systems Engineering, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan.
Article Synopsis
- Indano[60]fullerene bromide is an important intermediate in making indano[60]fullerene ketone, a derivative that can easily evaporate.
- Researchers utilized aqueous hydrobromic acid to create a consistent and high-yielding reaction process.
- A method for a scalable one-pot synthesis of indano[60]fullerene ketone from aryl[60]fullerenyl dimers was successfully demonstrated.
Palladium-Catalyzed Three-Component 1,4-Alkoxyarylation Reaction of [60]Fullerene.
J Org Chem
March 2022
Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.
The palladium-catalyzed three-component alkoxyarylation reaction of [60]fullerene with primary/secondary alcohols and aryl iodides generates a series of 1,4-(alkoxy)(aryl)[60]fullerene derivatives. Plausible reaction pathways for the formation of 1,4-(alkoxy)(aryl)[60]fullerenes are proposed. In addition, the electrochemical properties of the synthesized 1,4-alkoxyarylation adducts are investigated.
View Article and Find Full Text PDFManganese(III) acetate-mediated synthesis of -substituted fulleropyrrolines the reaction of [60]fullerene with α-monosubstituted acetaldehydes and primary amines.
Org Biomol Chem
December 2021
Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia.
The simple one-step reaction of [60]fullerene with α-monosubstituted acetaldehydes and primary amines in the presence of Mn(OAc)·2HO under air conditions afforded a series of novel -substituted fulleropyrrolines with trisubstituted CC bonds in moderate to good yields. The addition of Mn(OAc)·2HO played a crucial role in the successful synthesis of -aryl fulleropyrrolines with trisubstituted CC bonds, which would be extremely difficult to prepare by known methods as a result of the decreased nucleophilicity of arylamines due to the p-π conjugation effect. Intriguingly, arylamines displayed abnormally higher reactivity as compared with non-arylamines in the current reaction system by the observation of obviously decreased equivalent of Mn(OAc)·2HO, higher product yields, and lower reaction temperature probably due to the radical reaction mechanism initiated by Mn(OAc)·2HO.
View Article and Find Full Text PDFPalladium-Catalyzed Three-Component Tandem Coupling-Carboannulation Reaction Leading to Polysubstituted [60]Fullerene-Fused Cyclopentanes.
Org Lett
January 2020
Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, School of Chemistry and Chemical Engineering , Henan Normal University, Xinxiang , Henan 453007 , China.
The first example of transition-metal catalyzed multicomponent carboannulation of [60]fullerene has been developed. [60]Fullerene, 2-(2,3-allenyl)malonates, and (hetero)aryl iodides undergo a Pd(0)-catalyzed tandem coupling-carboannulation process for regioselective access to novel polysubstituted [60]fullerene-fused cyclopentane derivatives with a wide range of substrate scope and high functional group compatibility. A plausible mechanism involving the formation of a fullerene-π-allylpalladium complex with the characteristic of a fullerene cation as a key intermediate has been proposed.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!