I have a terminal olefin bearing an allene moiety(they're quite far apart) in hand.
I'm meant to functionalise this olefin to enones or vinyl esters.
But, as expected, its coupling with acrylates by Grubbs metathesis is somewhat risky due to its undesired metathesis with the allene moiety.
Can anyone suggest other possible routes to functionalise this olefin? at least to vinyl halide or vinyl tin? (for further activation?)
Thank you!
If the allene is internal, there may be a chance the steric effect may allow the terminal olefin to react preferentially. You may need to try various catalysts to get the optimal one.
The other way will be to use an aldehyde instead of the alkene, for Wittig type reaction, or alkyne for Schwartz hydrozirconation. Alkyne metathesis may also be possible followed by selective reduction of the alkyne.
@Eugene Yang Thank you. I was looking for some ways such as Hiyama and Stille couplings to keep stable vinyl Si/Sn for continued steps. But I think I should try direct Grubbs metathesis first as you said.
You can check out the MIDA stabilised boronates developed by Martin Burke's group as well.
http://www.nature.com/nchem/journal/v8/n11/abs/nchem.2571.html
other relevant references are within the article
- Badges
- Science topic
- Similar topics
- Physical Sciences
- Physical Phenomena
- Luminescence
- Fluorescence