Thursday, January 17, 2013

Welcome, Blog Syn!

I have other posts scheduled for today, but they're being written. I want to take a moment and point you to See Arr Oh's project with katmatcher, BRSM and Organometallica called "Blog Syn". They're looking at an interesting Fe/S-catalyzed benzimidazole synthesis that was recently published in J. Am. Chem. Soc. 

After 3 separate people (BRSM, katmatcher and OM) in 3 separate laboratories have done the chemistry in the paper, they've labeled it "moderately reproducible." 

It'll be interesting to see how they verbally describe papers from here on out. I suggest a few other terms to be introduced, including "totally sketchball", "rock solid" and the ever-popular "This reaction is so rugged my 90-year-old grandma could run it." 

I have 3 things to say about it:
  • This is awesome. It's really important and good for the wider chemistry community. More people should be telling each other their results like this. It's beautifully documented, too. 
  • Vinylogous is right; this needs established PI support for it to thrive as well as it should. While there are definitely future (and current!) assistant professors reading about this and thinking about it, I think that a couple of brave associate and full professors throwing their weight behind this now would be fantastic. 
  • I think that this would be a perfect project for senior theses (and maybe as part of a candidacy exam?) 
Readers, please go over there, read and comment. Also, thoughts on how to make this better? Got a procedure to vet? 

10 comments:

  1. CoulombicExplosionJanuary 17, 2013 at 1:18 PM

    I was once at a seminar given by a PI where he described a particular reaction as being "full professor chemistry" - meaning that it was sufficiently robust that even a full professor could run it.

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  2. I'm not sure many senior chemistry majors would view this activity as a particularly interesting thesis project--

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  3. Anon@2:14 back again: but where it would work nicely is in an upper-division synthesis course w/laboratory.

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  4. Benzylic Oxidation with IBX: JACS 124 (10), 2245-2258 (2002)!

    0% conversion for multiple substrates with multiple chemists.

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    1. Have you tried making fresh IBX? That stuff can be a bit tricksy sometimes... Just be careful when it gets to the explosive stage - it's fine if you don't bash it around/grind it up.

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    2. That might be a worthwhile one, because I believe Jin Quan Yu (not one of the authors) was complaining about that paper not being cited often enough as background in some CH oxidation papers.

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  5. Yes, multiple commercials lots and self-made. As of 2-3 years ago, a ChemFinder search by structure and IBX showed returned nothing beyond the original publication. No access currently, can anyone verify?

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    1. Can you suggest a specific reaction in the paper that does not work for you? One with relatively common starting materials would be helpful.

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    2. It's been awhile, but pretty sure we tried p-bromotoluene, as GC-MS with an autosampler was fastest for lots of rxs. We even made the IBX (multiple sets of hands) after failing with commercial sources.

      Can you confirm my general failure in Chemfinder with Ar-CH3 + IBX -----> Ar-CHO ?

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    3. Woah, just found this. I was attempting an IBX ox of 4-bromotoluene like 4 months ago. Never worked.. Also had a couple people in our lab try making IBX and still failed.

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