[Reddart]

I am thinking about coupling a secondary amine with (bromophenylethynyl)trimethylsilane using Pd2(dba)3,(tBu)3P, NaOtBu,toluene, but I'm not sure if the TMS will be stable enough. Should I be worried?

[wildfyr]

Yes I think you should be worried. TMS groups are curiously similar to protons in behavior. I know there are two typical TMS-alkyne deprotection techniques: a fluoride source like TBAF or K₂CO₃ in methanol which will produce low amounts to MeO^- to deprotect the alkyne. I could not find an example on sicifinder of tert butoxide being used around a phenylethynyl trimethylsilane. Its worth a small scale hail mary attempt though since t-butoxide is pretty different from methoxide.

[Reddart]

Im thinking that maybe I can get away with it since the reaction is in toluene, and the reaction generally has been reported to go at ambient temperatures. I'll give it a try and report what happens.

[Reddart]

I did find a patent with similar conditions, though of course that can be suspect.