A New Paradigm for Carbon-Carbon Bond Formation: Aerobic, Copper-Templated Cross-Coupling

摘要

We describe herein a mechanistically unprecedented system for the construction of carbon—carbon bonds: the copper-templated coupling of a thioorganic and a boronic acid that is rendered catalytic under aerobic conditions. This new reaction type evolved from mechanistically distinct earlier transformations discovered in this laboratory and subsequently extended in others: the anaerobic coupling of a wide range of thioorganics with either boronic acids or organostannanes that require the presence of catalytic quantities of a palladium source and stoichiometric quantities of a Cu carboxylate. In this communication, we reveal the unique attributes of the copper-catalyzed, aerobic reaction system applied to the formation of ketones by the coupling of thiol esters with boronic acids at neutral pH.