An efficient palladium-catalyzed reaction of [60]fullerene with benzoic acids via carboxylic acid group-directed C-H bond activation is achieved. The obtained [60]fullerene-fused lactones can undergo a retro Baeyer-Villiger reaction to provide [60]fullerene-fused ketones via apparent reduction in the presence of triflic acid. A representative ketone product obtained by the reduction reaction can be employed as an overcoating layer for the electron-transporting layer in an n-type perovskite solar cell.
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Synthesis of [60]Fullerene-Fused Lactones via Carboxylic Acid Group-Directed C-H Bond Activation and Further Retro Baeyer-Villiger Reaction.
Org Lett
June 2024
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, P. R. China.
An efficient palladium-catalyzed reaction of [60]fullerene with benzoic acids via carboxylic acid group-directed C-H bond activation is achieved. The obtained [60]fullerene-fused lactones can undergo a retro Baeyer-Villiger reaction to provide [60]fullerene-fused ketones via apparent reduction in the presence of triflic acid. A representative ketone product obtained by the reduction reaction can be employed as an overcoating layer for the electron-transporting layer in an n-type perovskite solar cell.
View Article and Find Full Text PDFElectrosynthesis of Decorated Basket Molecules: [60]Fullerene-Fused 12-Membered Macrolactones.
Org Lett
August 2022
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.
The electrosynthesis of decorated basket molecules, that is, [60]fullerene-fused 12-membered macrolactones, has been achieved efficiently for the first time by the electrochemical reduction of [60]fullerene-fused 6-membered lactones and subsequent ring expansion with 1,2-bis(1-bromoalkyl)benzenes. The observed isomeric distributions of the obtained macrolactones are elucidated by theoretical calculations. The product structures have been firmly established by single-crystal X-ray analyses.
View Article and Find Full Text PDFRetro Baeyer-Villiger reaction: thermal conversion of the [60]fullerene-fused lactones to ketones.
Chem Commun (Camb)
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 conversion of the [60]fullerene-fused lactones to ketones with triflic anhydride as an unusual reductant under aerobic conditions has been achieved in excellent yields. The present thermal retro Baeyer-Villiger reaction from lactones to ketones has no precedents. In addition, the unique ring-opened peroxy [60]fullerene derivatives can be obtained by the electrochemical reactions of the synthesized [60]fullerene-fused ketones.
View Article and Find Full Text PDFA copper-promoted synthesis of epoxy-bridged [60]fullerene-fused lactones and further derivatization.
Chem Commun (Camb)
July 2021
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. and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. China.
Article Synopsis
- A new method has been developed that uses copper to promote a reaction between [60]fullerene (C60) and two identical α-oxocarboxylic acids, resulting in the creation of unique epoxy-bridged C60-fused lactones.
- This process also allows for the transformation of these lactones into rare compounds like epoxy-bridged C60-fused hemiacetals and bicyclic-fused 1,2,3,4-adducts.
- The structures of these new compounds have been confirmed using single-crystal X-ray crystallography, and possible reaction mechanisms for the synthesis have been suggested.
Electrochemical Benzylation of [60]Fullerene-Fused Lactones: Unexpected Formation of Ring-Opened Adducts and Their Photovoltaic Performance.
Org Lett
September 2019
CAS Key Laboratory of Soft Matter Chemistry, 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.
Electrochemical benzylation of [60]fullerene-fused lactones with different motifs unexpectedly affords three types of ring-opened benzylated adducts under different conditions. Both [60]fullerene-fused δ- and γ-lactones can be benzylated to generate ring-opened mono- and bis-benzylated adducts in good yields. In addition, representative fullerene products have been applied as efficient electron-transport materials in perovskite solar cells.
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