Transition-metal-free and chemoselective NaO(t)Bu-O2-mediated oxidative cleavage reactions of vic-1,2-diols to carboxylic acids and mechanistic insight into the reaction pathways.

A method for efficient oxidative cleavage of vic-1,2-diols using a NaO(t)Bu-O2 system resulted in the formation of carboxylic acids in high yields. The present protocol is an eco-friendly alternative to a conventional transition-metal-based method. This new strategy allows large-scale production with nonchromatographic purification while also suppressing competitive reaction pathway such as benzilic acid rearrangement.