Carbon−Gold Bond Formation through [3 + 2] Cycloaddition Reactions of Gold(I) Azides and Terminal Alkynes

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.