I understand that fluorinated compounds are important in medicinal chemistry and such, but look at this reaction. You start with a stannane and then use two equivalents of silver triflate. So let's review. Three equivalents of heavy metals to make one C-F bond. This is not a great reaction. So how in the hell did it get accepted?
Oh that's how. Nice.
Oh that's how. Nice.
5 comments:
The secret to getting something into an ACS journal is fellatio technique. Fellate or perish.
I'm surprised you like that so little. It's not interesting outside the realm of people who give a shit about fluorine chemistry, but as far as I know there are only a few ways to put one on, and now there's one more.
Obviously this is not going to be a great way to do it, but with the current surge in PET I bet a few folks will be psyched they can tack 18-F on at the last step in only 20 min, even if it is swimming in garbage at the end of the reaction. That's what HPLC is for.
And yes, fellating is the true way to the top.
I neglected to mention that one of the ways to put a fluorine on an aromatic ring is the Balz-Schiemann reaction, one of my favorite named reactions for no reason other than the name itself.
Yeah, a 20-min reaction time is nice for PET, but how long does the reaction to make the DABCO-F reagent guy take? This paper sucks.
Actually, I think it would matter more whether the fluorines of the two hexafluorophosphates are exchangeable. It would be pretty shitty if you needed 13 eq of hot fluorine.
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