[Guitarmaniac86]

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?

[phth]

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.

[phth]

P.S.,

Why not tosyl chloride/fluoride and pyridine?