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Topic: ethynyltrimethylsilyl stable to Hartwig (NaOtBu)?  (Read 3508 times)

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Offline Reddart

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ethynyltrimethylsilyl stable to Hartwig (NaOtBu)?
« on: May 17, 2018, 03:57:01 PM »
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?

Offline wildfyr

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Re: ethynyltrimethylsilyl stable to Hartwig (NaOtBu)?
« Reply #1 on: May 17, 2018, 04:32:49 PM »
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.
« Last Edit: May 17, 2018, 04:45:11 PM by wildfyr »

Offline Reddart

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Re: ethynyltrimethylsilyl stable to Hartwig (NaOtBu)?
« Reply #2 on: May 17, 2018, 08:07:20 PM »
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.

Offline Reddart

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Re: ethynyltrimethylsilyl stable to Hartwig (NaOtBu)?
« Reply #3 on: May 21, 2018, 04:00:45 PM »
I did find a patent with similar conditions, though of course that can be suspect.

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