Carbon-gold bond formation propels a growing number of homogeneous catalyses, but the C-Au bond formation itself is comparatively underinvestigated. Reported here are C-Au bond-forming reactions that result from [3 + 2] cycloaddition of (triphenylphosphine)gold(I) azide to terminal alkynes. The reaction proceeds with the preformed azide complex or, in situ, by reaction of the corresponding gold(I) alkynyl with trimethylsilyl azide in the presence of protic solvents. This metal-mediated cycloaddition is analogous to the Huisgen dipolar addition of azides and alkynes and provides access to new classes of gold-bearing compounds and materials.

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