Coupling triisopropylsilyl acetylene

In certain cases copper catalyzed processes might also be used for the N-alkynylation of azoles. Methyl indole-3-carboxylate was coupled with 1-bromo-2-triisopropylsilyl-acetylene in the presence of a copper-phenantroline catalyst to give the desired 1-ethynylindole derivative in excellent yield (6.74.),105... 

The most commonly used protecting group for acetylenes is the trimethylsilyl (TMS) group.f Thus, commercially available trimethylsilylacetylene provides an excellent starting material for the synthesis of aryl and alkenyl acetylenes. Triisopropylsilyl groups are also useful for the step wise deprotection with TMS groups (Scheme 37). Cross-coupling of aryl or alkenyl halides with trimethylsilylacetylene proceeds in the presence of a Pd catalyst and Cul, followed by treatment with dilute aqueous or in... 

The copper-catalyzed cross-coupling of TIPS-acetylene with bis iodo 1,6-heptadiyne generated a triisopropylsilyl-capped tetrayne in good yield (eq 15). ... 

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