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Issue 50, 2014
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The first peripherally masked thiol dendrimers: a facile and highly efficient functionalization strategy of polyester dendrimers via one-pot xanthate deprotection/thiol–acrylate Michael addition reactions

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Abstract

Introducing multiple reactive functional groups at the periphery of dendrimer materials presents considerable challenges if the functionality is able to self-react. An efficient and facile approach to introducing masked thiols at the surface of polyester dendrimers is presented. One-pot, deprotection/thiol–acrylate Michael addition from the xanthate-functional dendritic substrates (generation zero to two) has been achieved for the first time, with high efficiency demonstrated using three acrylates of varying chemistry and avoiding disulfide formation.

Graphical abstract: The first peripherally masked thiol dendrimers: a facile and highly efficient functionalization strategy of polyester dendrimers via one-pot xanthate deprotection/thiol–acrylate Michael addition reactions

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Publication details

The article was received on 22 Dec 2013, accepted on 26 Feb 2014 and first published on 27 Feb 2014


Article type: Communication
DOI: 10.1039/C3CC49704F
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Citation: Chem. Commun., 2014,50, 6574-6577
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    The first peripherally masked thiol dendrimers: a facile and highly efficient functionalization strategy of polyester dendrimers via one-pot xanthate deprotection/thiol–acrylate Michael addition reactions

    S. E. R. Auty, O. Andrén, M. Malkoch and S. P. Rannard, Chem. Commun., 2014, 50, 6574
    DOI: 10.1039/C3CC49704F

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