Selecting reactions and reactants using a switchable rotaxane organocatalyst with two different active sites.

نویسندگان

  • Jack Beswick
  • Victor Blanco
  • Guillaume De Bo
  • David A Leigh
  • Urszula Lewandowska
  • Bartosz Lewandowski
  • Kenji Mishiro
چکیده

The activation mode of a rotaxane-based organocatalyst with both secondary amine and squaramide catalytic units can be switched with acid or base. The macrocycle blocks whichever of the catalytic sites it is positioned over. The switchable rotaxane catalyst generates different products from a mixture of three building blocks according to the location of the macrocyclic ring in the rotaxane.

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منابع مشابه

Selecting reactions and reactants using a switchable rotaxane organocatalyst with two different active sites† †Electronic supplementary information (ESI) available: Synthetic procedures and characterisation data. See DOI: 10.1039/c4sc03279a Click here for additional data file.

Synthetic catalysts have previously been developed where a stimulus can be used to turn the catalytic activity ‘on’ or ‘off’ or to change the stereochemical outcome of a reaction. Here we report on an articial system that can switch between two different modes of organocatalysis, each promoting a different chemical transformation. The result is a molecular catalyst that can be used to produce ...

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Semi - Empirical Study of a pH - Switchable [ 2 ] Rotaxane

Semi-empirical (AM1) electronic structure calculations are reported on a pH-switchable [2] rotaxane whose synthesis was reported in [Angew. Chem. Int. Ed., 36 (1997) 1904]. The [2] rotaxane possesses two cationic binding sites, with different affinities toward dibenzo [24] crown-8 (the ring component of the [2] rotaxane) depending upon the pH of the system. The computational results capture thi...

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A neutral redox-switchable [2]rotaxane.

A limited range of redox-active, rotaxane-based, molecular switches exist, despite numerous potential applications for them as components of nanoscale devices. We have designed and synthesised a neutral, redox-active [2]rotaxane, which incorporates an electron-deficient pyromellitic diimide (PmI)-containing ring encircling two electron-rich recognition sites in the form of dioxynaphthalene (DNP...

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عنوان ژورنال:
  • Chemical science

دوره 6 1  شماره 

صفحات  -

تاریخ انتشار 2015