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Copper-Catalyzed C[BOND]C Coupling of Thiol Esters and Boronic Acids under Aerobic Conditions



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Getting rid of palladium: Thiol esters can be cross-coupled with boronic acids to generate ketones at neutral pH by using a CuI-oxygenate catalyst under aerobic and Pd-free conditions (see scheme; S-pendant=NHtBu thiosalicyclamide). The mechanistically unique coupling is likely to proceed by a preorganized, higher oxidation state Cu species that relies on appropriately positioned ligating S-pendant groups on the thiol ester and on an additional equivalent of the boronic acid.

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