Deoxofluorination of carboxylic acid #organic_chemistry

Now I moved from medchem team to comp.chem team but still have interest against organic chemistry.

Today I found interesting article in JOC.

The article describes about method for synthesizing of trifluoro BB with SF4.
https://pubs.acs.org/doi/10.1021/acs.joc.9b02596

The elegant work was published from researcher of ENAMINE.

As you know enamine has huge amount of unique building blocks for Drug Discovery. Several years ago I had opportunity to visit Enamine. It was well organized and there are many high skilled researchers.

OK, back to the article.

The author found suitable reaction condition for converting aliphatic carboxylic acid to trifluoro methyl group.

And the important thing is that the reaction proceed mild condition (55 degree), keep substrate stereo chemistry, wide functional group tolerance with good yield.

The key point is that small amount of water addition. In the revious method, liquid HF was used for reaction solvent. HF is highly toxic so it is not suitable solvent for common labo work I think.

Of course SF4 is also toxic reagent. To handle the reagent, it is required safety facility.

However in Scheme 4 shows that wide range of applicability of the reaction condition.

And from experimental section, the reaction can conduct gram scale.

It is very useful for medicinal chemistry I think. New building block synthesis is very exiting work for me.

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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