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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?

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.


Why not tosyl chloride/fluoride and pyridine?


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