Biomimetic functional models of the mononuclear copper enzyme galactos
e oxidase are presented that catalytically oxidize benzylic and allyli
c alcohols to aldehydes with O-2 under mild conditions, The mechanisti
c fidelity between the models and the natural system is pronounced. Mo
dest structural mimicry proves sufficient to transfer an unusual ligan
d-based radical mechanism, previously unprecedented outside the protei
n matrix, to a simple chemical system.