A catalyst-free
and transition-metal-free method for the synthesis
of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation
of various internal alkynes, especially more challenging aryl-alkyl
acetylenes, proceeded smoothly with inexpensive, easily handled, and
commercially available potassium persulfate and an ambient air balloon,
achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile,
mechanistic studies indicated a radical process, and the two oxygen
atoms in the 1,2-diketons were most likely from persulfate salts and
molecular oxygen, respectively, rather than water.
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