Copper-Catalyzed Oxidative Cleavage of the C-C Bonds of β-Alkoxy Alcohols and β-1 Compounds.

Copper-catalyzed aerobic oxidation conditions were employed to promote the C-C bond cleavage of β-alkoxy alcohols and β-1 compounds (lignin model compounds). Besides these compounds, various 1,2 and 1,3-diols were successfully converted to aldehydes. We propose the Cu(I)-catalyzed mechanism explaining the C-C cleavage of these 1,2 and 1,3-dihydroxy compounds and β-alkoxy alcohols based on XPS data. Although our reaction conditions do not include large excess of bases and elaborated ligand-modified catalysts, copper salts with/without Me-TBD show good catalytic activities for C-C bond cleavage of various lignin model compounds.