Synthesis of carboxylic acid derivatives under conditions of acid catalysis from carbon monoxide, olefins, and acylating compounds

Author(s):  
Yang Yung Ping ◽  
K. V. Puzitskii ◽  
Ya. T. �idus
2009 ◽  
Vol 45 (6) ◽  
pp. 567-573 ◽  
Author(s):  
SANTE CAPASSO ◽  
FILOMENA SICA ◽  
LELIO MAZZARELLA ◽  
GIANFRANCO BALBONI ◽  
REMO GUERRINI ◽  
...  

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Fang-Fang Tan ◽  
Xiao-Ya He ◽  
Wan-Fa Tian ◽  
Yang Li

AbstractCleavage of C–O bonds in lignin can afford the renewable aryl sources for fine chemicals. However, the high bond energies of these C–O bonds, especially the 4-O-5-type diaryl ether C–O bonds (~314 kJ/mol) make the cleavage very challenging. Here, we report visible-light photoredox-catalyzed C–O bond cleavage of diaryl ethers by an acidolysis with an aryl carboxylic acid and a following one-pot hydrolysis. Two molecules of phenols are obtained from one molecule of diaryl ether at room temperature. The aryl carboxylic acid used for the acidolysis can be recovered. The key to success of the acidolysis is merging visible-light photoredox catalysis using an acridinium photocatalyst and Lewis acid catalysis using Cu(TMHD)2. Preliminary mechanistic studies indicate that the catalytic cycle occurs via a rare selective electrophilic attack of the generated aryl carboxylic radical on the electron-rich aryl ring of the diphenyl ether. This transformation is applied to a gram-scale reaction and the model of 4-O-5 lignin linkages.


ChemCatChem ◽  
2018 ◽  
Vol 11 (1) ◽  
pp. 383-396 ◽  
Author(s):  
S. M. A. Hakim Siddiki ◽  
Md. Nurnobi Rashed ◽  
Md. Ayub Ali ◽  
Takashi Toyao ◽  
Pussana Hirunsit ◽  
...  

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