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Issue 27, 2018
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Selective activation of organocatalysts by specific signals

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Abstract

Reminiscent of signal transduction in biological systems, artificial catalysts whose activity can be controlled by physical or chemical signals would be of high interest in the design of chemical systems that can respond to their environment. Self-immolative chemistry offers a generic method for the development of catalysts that can be activated by different signals. To demonstrate the versatility of that concept, we synthesized organocatalysts that can be activated by three different signals and that can be used to control two different reactions. In this way the organocatalyst proline is designed as a pro-catalyst that is activated either by the chemical signal H2O2, by light or by the enzyme penicillin acylase. The pro-catalysts were used to exert temporal control over the rate of an aldol reaction and a Michael reaction.

Graphical abstract: Selective activation of organocatalysts by specific signals

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Publication details

The article was received on 04 May 2018, accepted on 19 Jun 2018 and first published on 20 Jun 2018


Article type: Edge Article
DOI: 10.1039/C8SC02019A
Citation: Chem. Sci., 2018,9, 5999-6005
  • Open access: Creative Commons BY-NC license
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    Selective activation of organocatalysts by specific signals

    C. Maity, F. Trausel and R. Eelkema, Chem. Sci., 2018, 9, 5999
    DOI: 10.1039/C8SC02019A

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

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