Wang X1, Chen RX1, Wei ZF1, Zhang CY1, Tu HY1, Zhang AD1.
J Org Chem. 2016 Jan 4;81(1):238-49. doi: 10.1021/acs.joc.5b02506. Epub 2015 Dec 15.The chemoselective transformation of diarylethanones via either aerobic oxidative cleavage to give arylmethanoic acids or tandem aerobic oxidation/benzilic acid rearrangement/decarboxylation to give diarylmethanones has been developed. The transformation is controllable and applicable to a broad spectrum of substrates and affords the desired products in good to excellent yields. Mechanistic insights with control reactions, (1)H NMR tracking, and single-crystal X-ray diffraction reveal a complex mechanistic network in which two common intermediates, α-ketohydroperoxide and diarylethanedione, and three plausible pathways are proposed and verified. Read More