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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: derekb.lowe@gmail.com Twitter: Dereklowe

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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

« Arsenic Bacteria: Does The Evidence Hold Up? | Main | NASA's Arsenic Bacteria: A Call For Follow-Up Experiments »

December 8, 2010

Fluorination Without Tears. Or Panicked Shouts.

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Posted by Derek

One of the comments to this post brought my attention to this paper in JACS on a new fluorinating agent. I just finished writing a column on fluorinated drugs for Chemistry World, so the subject is on my mind.

I have to say, this looks like it could be a very useful reagent. I've never worked with any arylsulfur trifluorides, but that looks to change soon, since I'd guess that this stuff will shortly be commercialized. An air-stable, non-runaway reactive fluorinating reagent would hit the spot. It would be fine with me if I never open another bottle of DAST again, and my experiences with the likes of xenon difluoride haven't been wonderful, either. If anyone gets a chance to try this compound out, let us know if it's all it's billed to be!

Comments (7) + TrackBacks (0) | Category: Life in the Drug Labs


COMMENTS

1. A Nonny Mouse on December 8, 2010 11:55 AM writes...

132 pages of supplementary information......

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2. David Formerly Known as a Chemist on December 8, 2010 11:56 AM writes...

I'm not sure I understand your aversion to DAST, Derek. I never had any issues working with DAST, and always somewhat liked the clean, chlorinated-swimming-pool smell. On the few occasions I got a little DAST vapor up my nose, I felt "cleaned out", sort of like after eating some really hot mustard on my eggroll.

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3. dearieme on December 8, 2010 2:16 PM writes...

"xenon difluoride": happy days - my first university chemistry lecture was on The Reactions of the Inert Gases.

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4. Direct Arylator on December 9, 2010 11:42 AM writes...

These other reagents are already commercially available.

http://dx.doi.org/10.1021/ol902039q

Permalink to Comment

5. Tom Womack on December 9, 2010 12:56 PM writes...

Where would I go to find a synthesis of something like PhCH2SF5 ? The conditions in the Fluolead paper seem pretty vigorous (AgF2) and the sulphur only ends up with three fluorines ...

Googling gives me a badly-scanned translation of a Slovenian paper saying that C6H5SF5 was found as a rare contaminant in the reaction mix after low-pressure RF irradiation of a C6H6/SF6 mix, which isn't as good or extensible synthesis as I would really hope for.

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6. Bill on December 9, 2010 6:45 PM writes...

I have read the article on this new reagent called Fluolead. It is an amazing and very promising reagent. I just purchased this reagent from Oakwood Products. You can go to their website: www.oakwoodchemical.com A CAS # for this reagent is: 947725-04-4. Good luck!!!

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7. joseph pilates on December 23, 2011 12:58 PM writes...

eres una mierda

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