New fluolination reaction from JACS #memo #organicchemistry

Trifuloromethylation is useful reaction in drug discovery. Because CF3 and other fluorinated substituent are often used in drug like molecules. It is also useful that the reaction can conduct in asymmetric manner.

I read interesting article in JACS today published by Trost’s group. The URL of the article is below.
https://pubs.acs.org/doi/10.1021/jacs.9b06231

You can see abstract without account.

My boss when I was student liked pi-allyl palladium reaction named Tsuji-Trost reaction. So allyl halide based palladium coupling is familiar for me. But in the reaction allyl bromide is used for substrate. The article uses allyl-fuluoride as a substrate. It is key point of the reaction, it is well designed!

In the reaction TMS-Rf(Rf means CF3, F5Ph and some fluorinated substituent). Fluorine atom from allyl fuluoride activates the TMS-Rf reagent and the reaction proceeds well.

They used chiral ligand in the reaction so these reactions proceeds enantio selective.

You can see many examples in scheme2 and all reaction shows good yield and enantio selectivity. The example in the article was limited in cyclic allyl fuluride. I thought cyclic substrate is suitable for stereo selective reaction compared to acyclic compound.

Process of something new is very exciting for me. Not only drug discovery but also compound synthesis, reaction design and etc…. ;-)

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Published by iwatobipen

I'm medicinal chemist in mid size of pharmaceutical company. I love chemoinfo, cording, organic synthesis, my family.

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