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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

« A Structure From the Molecular Sponge | Main | Repurposing for Cervical Cancer »

March 7, 2014

Some New Reviews

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Posted by Derek

Walensky and Bird have a Miniperspective out in J. Med. Chem. on stapled peptides, giving advice on how to increase one's chances of success in the area. Worth checking out, unless you're at Genentech or WEHI, of course. The authors might say that it's especially worth reading in those cases, come to think of it. I await the day when this dispute gets resolved, although a lot of people awaited the day that the nonclassical carbocation controversy got resolved, too, and look how long that took.

And in Science, Tehshik Yoon has a review on visible-light catalyzed photochemistry. I like these reactions a lot, and have run a few myself. The literature has been blowing up all over the place in this field, and it's good to have an overview like this to keep things straight.

Comments (14) + TrackBacks (0) | Category: Chemical News


COMMENTS

1. Paul on March 7, 2014 12:09 PM writes...

What are currently the highest volume uses of visible light photochemistry in the chemical industry?

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2. leftscienceawhileago on March 7, 2014 2:26 PM writes...

Too bad there isn't some sort of awesome click photo catalytic reaction (something with specificity and that "really works").

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3. Anonymous on March 7, 2014 2:31 PM writes...

Wow, organic chemists have rediscovered photochemistry. But, now you can use visible light-sounds like an earth-shattering advance.

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4. Anonymous on March 7, 2014 2:58 PM writes...

@1 Food production? ;)

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5. Paul on March 7, 2014 3:32 PM writes...

@4. Heh.

I was wondering about processes that use large quantities (stoichiometric) of photons. There's a photochemical process like that for making caprolactam, but I don't know if it's still being used.

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6. Anonymous on March 7, 2014 3:55 PM writes...

Benzyl chloride production? I'm not sure what wavelength is used though.
I just read an OPR+D article about Artemisinin production, there's a singlet oxygen step and it's carried out on many 100s of kgs per batch.

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7. james on March 7, 2014 4:00 PM writes...

Paul, that is indeed an interesting question.

Photocatalysis works in flow reactions. But getting a light source into a reactor?

I would also be interested to hear if photocatalysis is considered useful outside academia at all.

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8. Curt F. on March 7, 2014 5:07 PM writes...

Chemjobber had a great post on the use of photochemistry in artemisenin synthesis.

http://chemjobber.blogspot.com/2014/03/process-wednesday-photooxidation-to-get.html

It's large scale by pharmaceutical-ish standards, but probably not by general chemical industry standards.

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9. 600nm on March 9, 2014 9:23 PM writes...

More importantly, why does every single Macmillan academic offspring work on visible light photoredox? Can't they be more original?

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10. ddd on March 10, 2014 9:04 AM writes...

@9:

Not much room to breakout in a field (organic synthesis) that is on the mature end. Look at organic textbooks from 20 years ago-not much has changed...

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11. InfMP on March 10, 2014 10:55 AM writes...

There are already too many reviews on photoredox:

10.1039/c3cs60188a
10.1002/adsc.201300751
10.1021/cr300503r
10.1002/anie.201200223
10.1002/ejoc.201300596
10.1002/ejoc.201101071

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12. Anonymous on March 10, 2014 10:58 AM writes...

@5 Caprolactam is the obvious one as you. I think the Toray process uses a 60 kW map.

It's very difficult to scale these things up without going to very powerful lamps. The Beer-Lambert law makes things difficult in batch. With Ru(bpy)3, more than 90% of light in absorbed within first 1 mm of your reaction vessel at typical concentrations (1 mM).

But even in flow you're going to need a very powerful lamp and lots of cooling. You also tend to get some polymer stuff that then absorbs creating more problems (flow can often overcome this as it doesn't tend to build up to quite the same extent as on batch).

Still a lot of work to do.

Will be interesting with the visible light stuff as currently the reactions are very dilute (probably due to Beer-Lambert law, Ru(bpy)3 has extinction coefficient of ~ 13,000) so not ideal for scale up

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13. Anonymous on March 10, 2014 11:00 AM writes...

This chemistry is really interesting and the potential is amazing, but why is this always called "photocatalyzed." The catalytic amount of material in there is a transition metal. There is superstoichiometric amount of light constantly saturating the system.

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14. Anonymous on March 10, 2014 5:35 PM writes...

@600nm: Yoon was with MacMillan before the advent of the group's work in photoredox chemistry. Photoredox began at Princeton in 2006/2007, I believe Yoon graduated from MacMillan's lab around 2002 and began this work in his independent career around 2005.

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