Gold-Catalyzed C(sp2 )-C(sp) Coupling by Alkynylation through Oxidative Addition of Bromoalkynes.

A gold(I)-catalyzed cascade cyclization-alkynylation of allenoates using alkynyl bromide to generate ß-alkynyl-γ-butenolides was investigated. Whereas alkynyl iodides afforded significant amounts of the homo-coupling of two lactone units, alkynyl bromides led to a selective reaction, and a broad functional group tolerance was observed. Under the optimized reaction conditions, it was possible to directly synthesize a large range of ß-alkynyl-γ-butenolides in moderate to good yields without the need for any external oxidant.