Oxidative C(OH)-C bond cleavage of secondary alcohols to acids over a copper catalyst with molecular oxygen as the oxidant

Selective oxidative cleavage of C-C bond is pivotal for producing functionalized molecules, useful for organic synthesis and biomass utilization. We herein report the oxidative C(OH)-C bond cleavage of secondary alcohols to acids over a copper/l, 10-phenanthroline complex with molecular oxygen as the oxidant. A wide range of secondary alcohols are converted into acids with up to 98% yields. More interestingly, it is effective for breaking up lignin model systems into acids, which is rarely achieved in previous studies. Density functional theory (DFT) calculations indicate a copper-oxo-bridged oxygen dimer is the active species for the C(OH)-C bond cleavage which is the rate-determining step for C-C bond. (C) 2017 Elsevier Inc. All rights reserved.