A Hemilabile NHC-Gold Complex and its Application to the Redox Neutral 1,2-Oxyarylation of Feedstock Alkenes

We describe a Au-I complex of a hemi-labile (C boolean AND N) N-heterocyclic carbene ligand that is able to mediate oxidative addition of aryl iodides. Detailed computational and experimental investigations have been undertaken to verify and rationalize the oxidative addition process. Application of this initiation mode has resulted in the first examples of exogenous oxidant-free Au-I/Au-III catalyzed 1,2-oxyarylations of ethylene and propylene. These demanding yet powerful processes establish these commodity chemicals as nucleophilic-electrophilic building blocks in catalytic reaction design.

Automated summary

We presented a Au-I complex of a hemi-labile (C boolean AND N) N-heterocyclic carbene ligand which can catalyze the oxidative addition of aryl iodides. Extensive computational and experimental investigations were performed to confirm and rationalize the oxidative addition process. The application of this initiation mode led to the first examples of exogenous oxidant-free Au-I/Au-III catalyzed 1,2-oxyarylations of ethylene and propylene. These challenging yet powerful processes establish these commodity chemicals as nucleophilic-electrophilic building blocks in catalytic reaction design.