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Nobel Prize in Chemistry Announced   

6 October 2010 29,491 views 48 Comments

Just a quick post-ette to congratulate Richard Heck of the University of Delaware, Ei-ichi Negishi of Purdue University, and Akira Suzuki of Hokkaido University for finally getting the recognition they deserve.  Decades of science have relied upon the palladium mediated reactions these guys pioneered, and it’s great to see that recognised.  I also feel that these are the correct chosen three in what is now a huge field, but I’m sure not everyone agrees.

Some links:  Nobel AnnouncementGuardian - BBC.

I’m also glad that the Graphene chemistry was acknowledged this year, making this year a double-chemistry Nobel Prize – two more than last year…

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48 Comments

  • HPCC says:

    Yeah. What about Stille and Sonogashira, while we’re at it? And Heck, being recognized in “cross-coupling” when there’s only an R-Pd-X species and an organic partner? (I know, this is nit-picking, but still…)

    Anyhow, I am SO VERY GLAD that finally, chemists (and even better, ORGANIC chemists!) are getting the Chemistry Nobel this year! Congrats!:D

  • R Stille says:

    I passed away some 20 years ago. No posthumous awards.

  • Sheep says:

    a well deserved prize for great chemistry!

  • PMP says:

    The fact that this prize was long overdue is clearly indicated in the ages of the awardees – Suzuki is an octagenarian and Heck and Negishi are 79 and 75, respectively! What a difference to the prize in physics this year – the awardees are 51 and 36 years old!

    The message: chemistry is for the old people, physics is the field where the young make discoveries. Of course we all know this is not true, but this is the message the people will get when you put these prizes side by side.

    This comment has nothing to do with the fact that I think both of these are highly deserved prizes and it is nice that the Nobel wheel has now turned back to chemistry!

    • European Chemist says:

      I thought the same. Might have to do with our tendency as Organikers to shoot each other on the foot. Heck (no pun intended), just read this blog comments which open with someone ranting on why A or B didn’t get the award. I, for once, was wondering whether the comittee was waiting for more people to die so they could narrow the prizes down further.
      I do, however, imagine some US-based chemists being a tad disappointed at not having occupied one of those 3 positions (though Heck’s spot and probably Suzuki’s are not really up for discussion).

  • InfMP says:

    I was hoping for Buchwald instead of Negishi, but I suppose people who are better able to rigorously exclude moisture and air than me have probably found Negishis quite useful.

    I think Lipshutz said it best (10.1021/ja906803t):

    “Although alkylzinc halides as nucleophiles are commonly regarded as the most reactive of partners … the conditions of their use in Pd
    catalysis are rigorously aprotic and not forgiving. Hence, prospects
    for effecting such reactions to any synthetically meaningful degree in
    the presence of moisture would typically be viewed as dim.”

    • European Chemist says:

      If you check the literature you’ll realise that Negishi used organoaluminum, organozirconium and even… organoboron reagents. I recall hearing his story that the boron derivatives were prohibitively expensive and so they could not afford to explore that as a methodology. They did a single example, but still published it a year or so before Suzuki. Hell, even Heck made a few stoichiometric experiments with vinylboronic acids and olefins. Looking back, what an opportunity they missed… though that can hardly be said from ANY Nobel laureate.

      • krest17 says:

        BTW in this paper Negishi-coupling was done in water, so it is not that moisture sensitive.

    • krest17 says:

      Hmm – nice when people cite you :-)

  • Just Another Chemist says:

    Negishi is well deserved to win the Nobel. He has developed much of the work in both Heck and Suzuki couplings. If I am not mistaken he also was pioneering in the catalytic cross coupling, along with Mizoroki, since Heck originally used stoichiometric conditions. The scope of the work that Negishi has done, along with his initial discoveries more than warrant his inclusion. The fact that he is on my committee has nothing to do with my endorsement;)

  • rhino says:

    I think it is ironic that in the midst of a ‘organic chemistry economic depression’ a indication of the importance of it is addressed. Good show! Too bad Tin is toxic. I’ll still take a Stille when the scale is small, the stakes are high, and I’m in the mood for a victory beer afterwards.

    God bless Heck. These recipients are highly deserving.

  • AIK Stockholm says:

    Absolutely fantastic. Bet Nobel Committee member Professor Bäckvall at Stockholm University has been buzzing for many weeks now. But of course this price gives the impression of being the last recognition of a field of organic chemistry that is on the verge of being “ready”.

    Organocatalysis next time? In 10 years that is..

  • stingray says:

    AIK – I doubt that “field” will be recognized. First, there is too much early precedent and the major industrial applications have already appeared prior to 2000 (merck phase transfer catalysis and of course the famous Hajos chemistry). Comparing the enabling nature of palladium to proline chemistry is like comparing kindergarten little league baseball to the yankees… Even 10 years ago it was clear that Palladium should win. Virtually no one uses proline and related stuff in industry as compared to Pd and metathesis that are used every day. Yes, there are lots of papers but I’d take one Buchwald JOC paper over 1000 proline garbage any day.

    In my opinion – Next up in organic synthesis will be more organometallics – N-C bond formation and C–H activation for example.

    • Ian says:

      ”Yes, there are lots of papers but I’d take one Buchwald JOC paper over 1000 proline garbage any day”

      LOL

      have you seen the latest org lett papers from Buchwald?

      A classic example that feeds proles like you

  • postdoc says:

    Anybody think Evans’ asymmetric aldol work will ever win? Do people think it’s worthy?

    • Ian says:

      Highly unlikely. An asymmetric synthesis Nobel has been awarded in the past 10 years and I doubt the commitee will go anywhere near it

      Organic wont see another recipient for a while IMO

    • HPCC says:

      In spite of its overall importance (historical and power as a method) in organic synthesis, I think it will never win, mostly because catalytic asymmetric C-C bond formation methods have emerged – one of them being the proline- and other organocatalysed methodologies. However, the very reason they emerged was because of Evans’ contribution to the field.

      • Ian says:

        Err, Evans contribution had nothing to do with the early proline work

        In fact, doesnt Hajosh-Parrish predate Evans by a good decade at least?

  • bad wolf says:

    I’m guessing HPCC meant Evans’ discoveries propelled other advances in the field. My old boss described two PIs, one slowly, rationally and methodically constructing a useful methodology; the other pulling random salts off the shelf to try as reagents. The second (KBS) wins the Nobel, the first (Evans) doesn’t. Just the way it goes. (No offense to Sharpless, who i do admire. But after having attended some of his talks that is about how he describes the SAE discovery.)

    As for the common “why not…” list, Sonogashira was maybe a result of the acetylene coupling being/appearing less biologically relevent? It would be interesting to compare citations for each of the Palladium Pioneers… Sonogashira may still have a shot if the application to useful materiala (OLEDs, eg) becomes more developed. And Hartwig and Buchwald et al just seem to be a second generation of research in the field, so they can wait until the first generation is suitably acknowledged.

    • HPCC says:

      You’re totally right. Evans and proline-catalysed aldol couldn’t be further remote, yet so close from each other. One’s stoichiometric, the other not. But proline- and amino-acid-catalysed methods exist because someone thought “there’s gotta be better than stoichiometric”.

      My comment is more meant to mean, because there are great methods, we should strive to look for even better ones.

      Just like the humbling moment of presenting my research proposals to my ex-supervisor, who said, great, but you’ll never ever get funded for trying to develop chiral chemistry using stoichiometric methods. That’s why Evans’, however great his method, is now slightly passé, for there are methods that don’t require 3 steps to form a bond asymmetrically (install chiral aux., do the aldol, remove the auxiliary). But don’t get me wrong, I have a tremendous amount of respect for Evans’ contribution to our field!! I wish I could see him talk before he dies – potentially of heart failure, I’m afraid… :-/

  • chirchir says:

    Did someone say Still died? Says who?

  • krest17 says:

    IMHO, C-H should be next (hope Shilov will be still alive).
    John Kenneth Stille (May 8, 1930 – July 19, 1989) was killed in the United Airlines Flight 232 crash at Sioux City, Iowa.

  • Cascade says:

    I strongly believe that organocatalysis the way it has been studied and reported so far, would ‘never’ win a Nobel prize.

  • optional says:

    We will have to wait a minimum of 15 years to see the impact of organocatalysis or B-H amination. I guess, now its all going to be Biochem, material chem, nano-chem, phys-chem, compu-chem. Unless, PI’s focus on basic research dealing with single topic (and have the proper funding for it), the number of years that will elapse will increase even further. Speaking of which, who does basic fundamental research other than organometallic people? How does one pick a topic that is going to change the field of O-chem. Life in academia is all about chugging papers and no one is willing to risk tenure or funding for doing basic research!!!!

  • European Chemist says:

    Interesting discussion about the worthiness of Organocatalysis for a Nobel Prize. There’s no doubt that few can remain indifferent to the “field” – even if nowadays it is increasingly difficult to narrow down what exactly is included in “organocatalysis”.
    It is also interesting to see a lot of animosity in the comments – mostly because most of the research groups working in organic chemistry regard organocatalytic research as, well, “not real chemistry”. It has to be recognised that the training of a Ph.D. scientist who spent 4 years running aldol reactions with a chiral organic compound as catalyst is, quite honestly, of a different nature of what you might expect in our discipline.

    • chinstrap says:

      You make a point about the animosity, but I aslo think “indifference” may be coupled to the over-hyping that is involved in the organocatalysis field.

      Proline-derived methodologies work well for many reactions involving many systems, however, O-Chem works in cycles and this domain (along with C-H activation)is popular at the moment for all comers.

      Frankly, I think some people are a little burned out with the saturation of closely related work. I don’t just mean the groups like List, MacMillan, etc. who actually attempt in depth research, I refer the groups that do “Look! Us too!” work that adds an incremental advancement and then ends up good journal for little insight to the science.

      • Sheep says:

        most methodologies are poor training grounds for organic chemists. Spending four years screening metal source, ligands and solvents to discover yet another iron-mediated cross-coupling might give a narrow scope of expertise in the end as well. Hence, total synthesis FTW!

      • European Chemist says:

        I was thinking about this the other day. Sure, Organocatalysis and C-H activation (much like Gold chemistry) are kind of overdone fashionable areas that will come and go. But the particular case of Organocatalysis is special, in that it suddenly aglomerated a lot of chemistry that was already there before (phase-transfer catalysis, some carbene chemistry and Denmark’s Lewis Base activation, to name a few) with all the chemistry that was to be developed afterwards under the same “roof”. In addition, it gave everyone an amazingly powerful “Buzzword” (like “Click Chemistry”) that everyone could start using to make their proposals sound sexier and obtain more funding.
        As much as I personally contest the utility and validity of this “field”, I for one think that organic chemists are terrible when it comes to “selling” or “marketing” their research to funding agencies and the public at large. Somehow these buzzwords and nice-sounding research areas give us something to hold on to.

        Just a thought.

        • Tot. Syn. says:

          I think part of the reason for why we have so many ‘buzzwords’ is the inaccessibility of organic chemistry to non-chemists. Even well trained scientists in other fields find it hard to appreciate. Take the example of the LHC at CERN: most of the public have heard of it, and have some sort of appreciation for what it’s there for – even if their grasp of quantum chromodynamics is less than glancing. It’s the big-smash-things-together-to-see-what-they’re-made-of-machine. So how the hell do you communicate the importance of frontier synthetic chemistry?

          Not that all physics communicates well – one major UK newspaper appears to believe that we already have graphene in our mobile phones…

  • Cascade says:

    I am all for total synthesis, BUT, Sheep you dont really know what you are talking about do you. These methodology guys actually give you the stuff that we use in our total synthesis!!!! So, they are in a way feedig us by doing fundamental research. Also, some total synthesis such as the later synthesis of englerin (personal opinion, request to see form educative angle) are a good examples of how a total chemist can do unproductive work.
    Yes, total synthesis is the best when seen from the training aspect, however, do not stab another fellow organic chemist in the back (read above comments)by ytour ridiculous rants

  • Fechemist says:

    Most total synthesis groups have their own methodologies to make certain building blocks. Without specialties, no novelty is there.
    Nobody wants to build a 10 feet rectangular lego building with only one color. That’s pain to watch and waste of time and money.

    Today, at Purdue, 2-day Negishi-Brown lecture was closed.
    Kozmin(UChicago), Koslowski(Upenn), Kabalka(UTN), Negishi(Purdue), Hoye(UMN), Coleman(OSU), Taylor(ND) were invited speakers. Inspired by all.

    • Fechemist says:

      Kozlowski(Upenn) <- corrected

      Prof. Kabalka showed a nice picture of three (Suzuki, Negishi, and himself). They were under H.C.Brown in late 1960s.

  • Yo says:

    For me the biggest mystery in Pd coupling is what contribution Miyaura made to the the “Suzuki” coupling. In the Japanese system many of the assistant professors working under the main guy have totally independent programs, but are compelled to include the main guy as an author because they provide the money and prestige and as a sign of respect. By the time the first “Suzuki” coupling was done, Miyaura had been Suzuki’s assistant professor for over 12 years. It is not inconceivable that Miyaura is actually more responsible for the coupling than the name commonly associated with it.

    I actually sometimes wonder if any Japanese professors have ever gotten credit for a Nobel Prize for an idea they had nothing to do with beyond providing labs and funding.

  • ZZZZZ says:

    zzzzz

    …Yo brings up an interesting point: Miyaura is indeed rumored to have been very important for the Suzuki reaction development.

    On the flip side, I was a little worried that Mizoroki might have been given consideration for the prize over others. I was glad to see that the committee chose Heck alone…

    zzzzz

    • frenchy says:

      they don’t say NaH is an oxidant, it simply plays the role of a base, and molecular oxygen is the oxidant

  • chirchir says:

    I totally got the names wrong … I misread what was written and had W. CLark Still and not Stille in my mind. Is he still alive?

  • frenchy says:

    Interesting points in the discussion on Miyaura/Suzuki, Mirozoki/Heck … it could have been an opportuniy to award younger chemists (when alive …). What about Banks and Bailey who described in 1964 (I&EC Prod. Res. Dev. 1964, 170-173) what would now be considered olefin metathesis ? They just did not use the term, like Mozart never said he was composing classical music.
    My bet for the next prize in organic chemistry would be Anastas/Trost/Sheldon for Green Chemistry.

  • striker says:

    Anybody see this paper? http://onlinelibrary.wiley.com/doi/10.1002/anie.201004704/abstract

    See third page, next to last paragraph. Copper does nothing.

    Sly way to avoid a retraction from Science. Only Science would let you republish a Friedel Crafts without doing a simple control study.

    Looks like the textbooks on Electrophilic aromatic substitution don’t need to be changed after all…

    What an embarrasment for cambridge.

    • rvich says:

      I worked in C-H functionalization and I suspected about simple Friedel-Crafts reaction. But some people unfortunately have open doors to journals, instead of retraction of science and angew appears…
      Reminds me the iron-with-copper catalysis…

  • TBS says:

    Wow. I guess people in Cambridge don’t know that a piv-protected aniline can be a meta director due to 1,3-strain.

    Never believed this work to begin with since all the substrates were engineered so that meta is the only possible product. The science paper should be retracted.

  • gang says:

    Why no new blog recently?

  • Nanaji says:

    congratulations to great Nobel winners,these 3 people are very great,because today many peoples used that reactions in total synthesis for coupling……………………Nance-2025.