October 04, 2022, 08:34:33 PM
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Topic: Fluorination  (Read 600 times)

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Offline Guitarmaniac86

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Fluorination
« on: November 15, 2021, 12:34:37 PM »
I need a sense check. I have three primary alcohols in a molecule, two tertiary alcohols, an amide and a lactone.


I want to fluorinate the primary alcohols with DAST or deoxofluor but I am concerned that the tertiary alcohols will probably fluorinate. Is this actually possible? I suspect that the primary alcohols will fluorinate much faster than anything else in my molecule.

I am also trying to avoid protecting groups because I want to limit the number of steps, but I do have a route with protecting groups ready to go.


Anyone have any insights on fluorination?
Don't believe atoms, they make up everything!

Offline phth

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Re: Fluorination
« Reply #1 on: January 02, 2022, 08:45:55 PM »
The question: is the reagent a lewis acid? Is the reagent strong enough of a lewis acid to form carbocations? If the reagent does not form carbocations (check tBuOH or similar stock chem), then it's probably fine. Seems like it is worth testing.

Offline phth

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Re: Fluorination
« Reply #2 on: January 02, 2022, 09:13:55 PM »
P.S.,

Why not tosyl chloride/fluoride and pyridine?

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