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Asymmetric Heterogeneous Catalysis   

17 July 2006 8,680 views 9 Comments


Glorius, Heitbaum and Escher. ACIE, 2006, 45(29), 2732; DOI: 10.1002/anie.200504212.

Add, stir and filter! Frank Glorius, who gave a superb lecture at the OMCOS-13 last year, has written a great review of Asymmetric Heterogeneous Catalysis in Angewandte. I’ve been meaning to blog this for ages, but as it’s been a quiet few days, now couldn’t be a better time!

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  • secret milkshake says:

    problem with magnetite-supported reagent is that magnetite is feromagnetic so it sticks to stirbar/bottom of the flask so you cannot use magnetic stirring.

    Just making the substituted BINAP and attaching it is awfull and negates the advantage of the catalyst recovery.

    The proper way of imobilising this kind of system is to use the TsDPHEN /RuCl2(cymene) version of the catalyst immobilised through the tosyl group. The Ru-catalyst with the mono-tosyl ligand works extremely well with aqueous sodium formate as source of hydrogen, no base is necessary.

    If one likes to be more creative, he can make Cl2RuCp* immobilised through the Cp* and use it likewise in place of RuCl2(cymene).

    Many immobilised catalysts are overrated for lab applications – they are much more expensive than unsupported version and often less catalyticaly active. Also, nobody likes to use a recycled stuff except for industry scaleup.

  • Tot. Syn. says:

    Good points. But in some cases, the solid-supported reagent is incredibly useful and beneficial, such as silica supported periodate. You just have to weigh-up the pros and cons.

  • secret milkshake says:

    What is periodate on silica used for?

  • Tot. Syn. says:

    Just as an example – if you have an allyl epoxyl alcohol, and you do an alkylation, you’ll get a diol. Depending upon the regiochemistry of the attack, you can get both the 1,2 and the 1,3 diol. If you (like me) only want the 1,3, it can be a tricky separation. However, pass the mixture through periodate on silica, the reaction is quick enough to cleave the 1,2 diol to the dialdehyde, and you can flush that off the column. The 1,3 diol stays intact, and you can then flush that off, nice and clean, using a more polar solvent. Just one great use.

  • ochemist says:

    wow, your blog looks really cool now. a very beautiful design…

  • Tot. Syn. says:

    Thankyou very much. I’m still tweaking the css, so you can expect it to change a little more. I’m just looking for a bit of consistancy between browsers… more difficult than it looks!

  • Klug says:

    If you’re the TBDPS of blogging, does this mean you’re acidic comment-insensitive?

  • Tot. Syn. says:

    Exactly. But I can’t use fluoride toothpaste, or I fall apart.

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