Researchers unlock coveted bond connection

Discussion in 'Chemistry' started by Plazma Inferno!, Sep 28, 2016.

  1. Plazma Inferno! Ding Ding Ding Ding Administrator

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    Researchers at Princeton University have introduced a long-awaited reaction capable of forming sp3-sp3 bonds whose presence increases a molecule’s complexity and its chances for clinical success as a drug candidate.
    The study detailed a mild and general method to couple sp3 carbon atoms – carbon centers defined by that fact that only single bonds connect them to their neighbors. Until now, this coveted reaction had resisted chemists’ efforts, even eluding transition metal catalysis, a powerful field that has enabled a staggering range of coupling reactions over the past 50 years.
    The reaction is a very unique way of approaching how you would join molecules together, and broadly expands the types of carbons you can connect.
    The team demonstrated the reaction’s generality as it proceeded smoothly with array of structurally diverse partners. Using this method, they also constructed the antiplatelet drug tirofiban in two steps from simple starting materials using their sp3-sp3 coupling reaction and another metallaphotoredox method recently developed in their lab. This example showcased the utility of their program for drug discovery though it holds potential for other industries as well.

    https://chemistry.princeton.edu/news/researchers-unlock-coveted-bond-connection

    Study: http://www.nature.com/nature/journal/v536/n7616/full/nature19056.html
     
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  3. Write4U Valued Senior Member

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    This may be of interest:
    http://www.ted.com/talks/oded_shose...m_medium=email&utm_content=button__2016-09-28
     
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  5. exchemist Valued Senior Member

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    I think that is rather different. Your link seems to relate to manipulating biochemistry. This thread, however, is about a specific organic synthesis step, viz. a new route to forming C-C bonds between sp3 hybridised carbon atoms. This is just synthetic organic chemistry, without harnessing natural biochemical pathways, of the type used by, for example, drug companies. The interesting thing here is that a lot of the conventional C-C bond formation reactions use sp2 hybridised carbon, e.g. carbonyl groups (>C=O) , while this doesn't.

    Exactly why this sp3-sp3 route is helpful is not something I can really answer, not having studied organic synthesis for over 40 years, although I note that the Nature paper indicates it may reduce the number of steps in certain syntheses and thereby improve yield (You always lose some material due to unwanted side reactions in any synthetic step).

    Anyway, it is an addition to the synthetic chemist's toolkit. Maybe someone else can comment in more detail.
     
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