The problem I have with the Stille coupling is that it always works. How do you like the sound of that? When Suzuki, Kumada, Negishi fail one after the other with certain troublesome substrates, Stille always comes to the rescue. Yields may vary, yields do vary, but there is always product. The problem then? Toxicity. Making Stille reagents is dangerous. Running Stille reactions is dangerous. Working up the product and taking care of Stille byproducts is dangerous. Especially at scale. Every little part of it, including that peculiar smell – toxic.

Dear geniuses out there, in academia, industry or wherever you hide, will you please come out and kick some life in the Hiyama coupling?

The day one can take a R-TMS (yes, straight TMS, no fiddling around with alkoxy-substituents) and make it as reactive as R-SnMe3 under cross-coupling conditions will be a good day. I hope I will live to see it.


3 Responses to My hate-love relationship with the Stille coupling

  1. Selective and general C-H/C-H coupling would be nice to replace the traditional X-couplings. Some progress, but not enough for your purposes yet I guess.

  2. milkshake says:

    I wonder if “supersilyl” group (TMS)3Si- would work as a R3Sn surrogate for Stille-like coupling (it does in case of Bu3SnH radical reduction).

  3. […] I did live to see it! The very reaction I requested here, a little more than a year ago. Check out this fantastico, shmantastico cross-coupling, in the […]

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