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December 19, 2011
Trifluoromethylation, The Easy Way?
Posted by Derek
In case people haven't seen it, this trifluoromethylation method from the MacMillan lab looks quite interesting. Now, not everyone loves the idea of sticking CF3 groups all over their molecules, and if you're a medicinal chemist you'll want to exercise restraint, but it's still an inarguably useful group. And the chemistry is interesting, too, using visible-light photoredox chemistry, an area that's been getting a lot of attention recently and seems pretty promising.
There's quite a list of reactions that have been done via this route, usually involving ruthenium or iridium catalysts and either fluorescent light or blue LEDs. (A trivia note: that ruthenium compound linked to looks more like good saffron powder, both in solid form and solution, than anything I've ever seen. It's all that Iranian food I get at home, I guess). Labs to watch include MacMillan's at Princeton, Corey Stephenson's at BU, and Tehshik Yoon's at Wisconsin, among others. Photochemistry has been a neglected field in many ways - perhaps taking it out of the ultraviolet and finding useful new reactions will slowly bring it back into the usual toolkit.
Comments (8)
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1. Chris on December 19, 2011 11:29 AM writes...
Don't forget PS Baran's method just a few months ago. http://www.pnas.org/content/early/2011/08/10/1109059108
Permalink to Comment2. marcello on December 19, 2011 1:07 PM writes...
CF3 group was loved by researchers in the NK-1 area... Exactly 3,5-phenyl substitution. "Hier ist das Hund begraben??"
Permalink to Comment3. anchor on December 19, 2011 2:18 PM writes...
A drug molecules can be changed to behave like Teflon as in CETP inhibitors from Merck. Lot of baggage with this group.
Permalink to Comment4. Chemjobber on December 19, 2011 2:24 PM writes...
Torcetrapib had 3 CF3s, right?
Permalink to Comment5. milkshaken on December 19, 2011 6:44 PM writes...
CF3 is for wimps. The real men put pentafluorosulfuranyl group and adamantane into their clinical candidate and formulate it as a soybean oil emulsion stabilized with cremophor
Permalink to Comment6. anon on December 19, 2011 7:41 PM writes...
Not sure of the utility of either MacMillan or Baren's methods. The thought of taking a molecule with several arenes and getting a mixture of trifluoromethylated isomers and hoping to be able to purify/separate is not appealing... There are other recent methods to consider instead (Hartwig & Buchwald have recent selective methods).
Permalink to Comment7. A Nonny Mouse on December 20, 2011 10:01 AM writes...
Don't forget that mefloquin (Lariam) has 2-CF3 groups- could explain its CNS side effects.
Permalink to Comment8. Anonymous on December 21, 2011 11:08 AM writes...
another new method today:
Permalink to Comment10.1021/ja209992w