Iron-catalyzed ring-opening of cyclic carboxylic acids enabled by photoinduced ligand-to-metal charge transfer

A decarboxylative ring-opening protocol of cyclic tertiary carboxylic acids via iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) is described. This reaction enables the preparation of 1, n -dicarbonyl compounds through the homolytic C-C bond cleavage of unstrained carbocyclic and h...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2022-07, Vol.24 (14), p.5553-5558
Main Authors: Tu, Jia-Lin, Gao, Han, Luo, Mengqi, Zhao, Lulu, Yang, Chao, Guo, Lin, Xia, Wujiong
Format: Article
Language:English
Subjects:
Carbonyl compounds
Carboxylic acids
Charge transfer
Covalent bonds
Green chemistry
Iron
Ligands
Peroxy radicals
Ring opening
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Summary:A decarboxylative ring-opening protocol of cyclic tertiary carboxylic acids via iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) is described. This reaction enables the preparation of 1, n -dicarbonyl compounds through the homolytic C-C bond cleavage of unstrained carbocyclic and heterocyclic ring systems. This method exhibits a lot of synthetic advantages including mild conditions, simple operation, and convenience of amplification. Mechanistic studies support the generation of peroxy radical species via oxygen capture followed by radical fragmentation. A decarboxylative ring-opening reaction of cyclic tertiary carboxylic acids via an iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) process is herein reported.
ISSN:1463-9262
1463-9270
DOI:10.1039/d2gc01738e