Alkynyl silanes can be easily hydrolyzed with TBAF like in the last step in the synthesis: enter image description here

How feasible is the hydrolysis of vinyl silanes with TBAF? Does it actually happen or some other routine must be used?


According to This article, vinylsilanes are stable in TBAF solutions, allowing other silyl groups to be removed selectively. They can be activated in the presence of TBAF using palladium similarly to a halide, though.

This link shows C2-trialkylsilylalkenes being cleaved with potassium t-butoxide, 16-crown-8 and TBAF. I'll look more thoroughly when I get to a computer, though.

I also found this example, but it had no reference, so I'll try to find one:

Example of protodesilylation of an alkene

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  • $\begingroup$ How to remove the silyl group? $\endgroup$ – RBW Feb 6 '16 at 22:52
  • $\begingroup$ Oh, you wanted a method to do it, too? That I'm not sure about. Looking at references, it doesn't look simple. See edit made. $\endgroup$ – SendersReagent Feb 6 '16 at 23:11
  • $\begingroup$ Interesting. Strong bases and mild acids can cleave them. $\endgroup$ – RBW Feb 7 '16 at 0:01
  • $\begingroup$ What search engine did you use? I couldn't find this. $\endgroup$ – RBW Feb 7 '16 at 17:35
  • $\begingroup$ I can't find it either, by using Google, I found the book. $\endgroup$ – SendersReagent Feb 7 '16 at 17:41

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