Homocoupling of benzyl pyridyl ethers visible light-mediated deoxygenation

The photocatalytic coupling of ethers is uncommon because of the challenges in breaking C-O bonds and low selectivity. Herein, we report a visible light-mediated deoxygenation homocoupling of benzyl pyridyl ethers via their pyridium salts. This approach enables C(sp 3 )-O bond homolysis under mild c...

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Published in:Chemical communications (Cambridge, England) England), 2023-09, Vol.59 (76), p.1149-11412
Main Authors: Chen, Jingtian, Wang, Fan, Li, Xiang, Wang, Lei, Yu, Wei, Sun, Keju, Yang, Jingyue
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Summary:The photocatalytic coupling of ethers is uncommon because of the challenges in breaking C-O bonds and low selectivity. Herein, we report a visible light-mediated deoxygenation homocoupling of benzyl pyridyl ethers via their pyridium salts. This approach enables C(sp 3 )-O bond homolysis under mild conditions. Mechanistic experiments support the radical nature of the reaction. This method is highly compatible with electron-withdrawing groups and has potential applications for drug precursor synthesis. The challenging cleavage of C-O bonds in ethers was successfully accomplished through a visible light-mediated deoxygenation process of benzyl pyridyl ethers via their corresponding pyridinium salts.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc03002d