About this Author
DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: Twitter: Dereklowe

Chemistry and Drug Data: Drugbank
Chempedia Lab
Synthetic Pages
Organic Chemistry Portal
Not Voodoo

Chemistry and Pharma Blogs:
Org Prep Daily
The Haystack
A New Merck, Reviewed
Liberal Arts Chemistry
Electron Pusher
All Things Metathesis
C&E News Blogs
Chemiotics II
Chemical Space
Noel O'Blog
In Vivo Blog
Terra Sigilatta
BBSRC/Douglas Kell
Realizations in Biostatistics
ChemSpider Blog
Organic Chem - Education & Industry
Pharma Strategy Blog
No Name No Slogan
Practical Fragments
The Curious Wavefunction
Natural Product Man
Fragment Literature
Chemistry World Blog
Synthetic Nature
Chemistry Blog
Synthesizing Ideas
Eye on FDA
Chemical Forums
Symyx Blog
Sceptical Chymist
Lamentations on Chemistry
Computational Organic Chemistry
Mining Drugs
Henry Rzepa

Science Blogs and News:
Bad Science
The Loom
Uncertain Principles
Fierce Biotech
Blogs for Industry
Omics! Omics!
Young Female Scientist
Notional Slurry
Nobel Intent
SciTech Daily
Science Blog
Gene Expression (I)
Gene Expression (II)
Adventures in Ethics and Science
Transterrestrial Musings
Slashdot Science
Cosmic Variance
Biology News Net

Medical Blogs
DB's Medical Rants
Science-Based Medicine
Respectful Insolence
Diabetes Mine

Economics and Business
Marginal Revolution
The Volokh Conspiracy
Knowledge Problem

Politics / Current Events
Virginia Postrel
Belmont Club
Mickey Kaus

Belles Lettres
Uncouth Reflections
Arts and Letters Daily
In the Pipeline: Don't miss Derek Lowe's excellent commentary on drug discovery and the pharma industry in general at In the Pipeline

In the Pipeline

« Deals of the Year in Biopharma (Bonus: Names That Can't Happen) | Main | Best Paper You Read This Year? »

December 19, 2011

Trifluoromethylation, The Easy Way?

Email This Entry

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) + TrackBacks (0) | Category: Chemical News


1. Chris on December 19, 2011 11:29 AM writes...

Don't forget PS Baran's method just a few months ago.

Permalink to Comment

2. 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 Comment

3. 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 Comment

4. Chemjobber on December 19, 2011 2:24 PM writes...

Torcetrapib had 3 CF3s, right?

Permalink to Comment

5. 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 Comment

6. 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 Comment

7. 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 Comment

8. Anonymous on December 21, 2011 11:08 AM writes...

another new method today:

Permalink to Comment


Remember Me?


Email this entry to:

Your email address:

Message (optional):

The Last Post
The GSK Layoffs Continue, By Proxy
The Move is Nigh
Another Alzheimer's IPO
Cutbacks at C&E News
Sanofi Pays to Get Back Into Oncology
An Irresponsible Statement About Curing Cancer
Oliver Sacks on Turning Back to Chemistry