Molecular Iodine Mediated Oxidation of Arylated α‐Carbonyl Sulfoxonium Ylides to 1,2‐Dicarbonyl‐Containing Compounds

This is the authors' abstract. We don't add key points for this paper.

Sulfoxonium ylides in recent years have proved to be versatile building blocks and have found applications in the synthesis of structurally diverse organic molecules. In this work, we report a new oxidative, molecular iodine‐mediated transformation on sterically encumbered arylated sulfoxonium ylides, which give access to 1,2‐dicarbonyl containing compounds. Twenty‐six examples have been realized (47–92 % yields), with structural diversity modified at two key sites on the sulfoxonium ylide reactants. Furthermore, the protocol benefits from the use of inexpensive molecular iodine to mediate the oxidation and, from a sustainability viewpoint, short reaction times (30 minutes), ambient temperature, and ethyl acetate as a greener reaction solvent. Experimental studies also gave insight to the mechanism of the reaction, involving DMSO as an oxygen source.