Reductive Cleavage of C-O Bond in Model Compounds of Lignin

A simple protocol for reductive cleavage of C-O bond in diaryl and aryl methyl ethers was reported, in which NaH served as a reducing agent and (KOBu)-Bu-t as a base and a radical initiator. The combination of NaH and (KOBu)-Bu-t displayed high efficiency for reductive cleavage of C-O bond in diaryl and aryl ethers (e.g., dibenzofuran, diphenyl ether, anisole) without the hydrogenation of the aryl rings, in the absence of any other catalysts or ligands at 140 degrees C, producing corresponding arenes and phenols. It was indicated that the reaction was under a radical mechanism.