Visible-light photoredox-catalyzed C-O bond cleavage of diaryl ethers by acridinium photocatalysts at room temperature.

ABSTRACT: Cleavage 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 c

SUBMITTER: Tan FF 

PROVIDER: S-EPMC7705023 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature