Synthesis of Alkenylgold(I) Compounds via Sequential Hydrozirconation and Zirconium to Gold Transmetalation

A new method for the synthesis of stereodefined organogold(I) compounds has been developed using an alkyne hydrozirconation and Zr to Au transmetalation sequence to prepare a series of functionally diverse (E)-alkenylgold(I) compounds that were inaccessible or unreported using other synthetic methods. This facile reaction sequence is complete in 4 h at ambient temperature and can employ commercially available starting materials. As part of this synthetic study, we also discovered an organogold compound that underwent an E to Z isomerization consistent with progression through a novel carbenoid pathway.