The first isolated examples of intermolecular oxidative addition of alkenyl and alkynyl iodides to Au are reported. Using a 5,5'-difluoro-2,2'-bipyridyl ligated complex, oxidative addition of geometrically defined alkenyl iodides occurs readily, reversibly and stereospecifically to give alkenyl-Au complexes. Conversely, reversible alkynyl iodide oxidative addition generates bimetallic complexes containing both Au and Au centers. Stoichiometric studies show that both new initiation modes can form the basis for the development of C-C bond forming cross-couplings.
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