Stereoselective oxidative coupling of ketones through a silybisenol ether intermediate is a powerful synthetic strategy. This reaction enables fragment coupling while creating vicinal stereocenters and a dissonant 1,4-dicarbonyl motif. Generally, oxidative coupling of ketones requires two stoichiometric equivalents of a metal oxidant such as cerium(IV) ammonium nitrate or copper(II) chloride. This work, however, shows that oxidative coupling products may be obtained in good yield by anodic and photocatalytic oxidation methods for more efficient and environmentally friendly processes. Notably, electrochemical oxidative coupling was successful with unconjugated, aliphatic substrates with high oxidation potentials. Photocatalytic means of coupling with [Ru(bpz)3][PF6]2 also showed promising results, giving good yields for the coupling of two aromatic ketones and the coupling aromatic ketones with aliphatic ketones. These methods provide an efficient means of oxidative coupling without stoichiometric metal oxidants for the synthesis of natural products and other complex organic molecules.

Electrochemical and photocatalytic oxidative coupling of ketones through a silylbisenol ether intermediate

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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