Hey guys, I could really use your help. I have devised this wonderful novel route that gives desired in much fewer steps than before – with a small caveat. The final compound has a tin too many. As I cannot show you exact structures, this image will have to suffice. R is actually lots of things, such as fused ring and so forth.
Lithiation followed by water or acid is out of the question, because of other labile groups. I spent some time in both SciFinder and Reaxys, and much to my surprise, I could not find a catalytic system that does what I want. Can this really be? I mean, I bet that if I would want to to use this material in a Stille coupling, at least 10 % of the protodestannylated product (which in our case is desired) would be one of the byproducts. I am surprised no one has figured out a way to do this catalytically – or my skills with our precious search tools are not what they once were. You tell me!
For aliphatic stannanes, I found this recipe in which you take your material in methanol and add TMSCl. Super-dry HCl thus forms in situ, and protodestannylates the product. But sp3 is not sp2.
If you happen to sit on a magic method or literature reference, the comment field is wide open! Thank you.