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December 8, 2010
Fluorination Without Tears. Or Panicked Shouts.
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 (9)
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College chemistry, 1983
The 2002 Model
After 10 years of blogging. . .
1. A Nonny Mouse on December 8, 2010 11:55 AM writes...
132 pages of supplementary information......
Permalink to Comment2. 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.
Permalink to Comment3. 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.
Permalink to Comment4. 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 Comment5. 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.
Permalink to Comment6. 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!!!
Permalink to Comment7. joseph pilates on December 23, 2011 12:58 PM writes...
eres una mierda
Permalink to Comment8. Stacy Velie on March 1, 2012 3:01 PM writes...
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Permalink to Comment9. Mei Brager on September 24, 2012 11:51 PM writes...
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