Synthesis of [60]Fullerene-Fused Lactones via Carboxylic Acid Group-Directed C-H Bond Activation and Further Retro Baeyer-Villiger Reaction.

Autor: Niu C; 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.; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China., Zhou DB; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China., Huang X; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China., Yin ZC; 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.; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China., Wang GW; 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.; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.; State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Jun 28; Vol. 26 (25), pp. 5300-5305. Date of Electronic Publication: 2024 Jun 17.
DOI: 10.1021/acs.orglett.4c01676
Abstrakt: 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.
Databáze: MEDLINE