Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions

Perspective gold-catalyzed transformations involving any carbon-heteroatom bond formation is reviewed. Liu and co-workers reported the formation of tricyclic spiro ketones 17/18 with PPh3AuOTf as catalyst. The use of peroxides in catalytic amounts to initiate the oxidation of alkenes with O 2 was first reported in 2005 and full conversion and 80% epoxide selectivity were achieved. Zhang and coworkers developed a carboalkoxylation procedure for terminal alkenes via oxidative gold catalysis, which provides access to various substituted O-heterocycles, including tetrahydrofurans. Asao and co-workers employed a smart strategy to transform alcohols to ethers, finding that alkyl esters containing an o-alkynylbenzoic acid as substituent, behave as alkylating agents in the presence of gold species.