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Issue 22, 2019
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Solid-phase synthesis of biocompatible N-heterocyclic carbene–Pd catalysts using a sub-monomer approach

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Abstract

Taking inspiration from the assembly of so-called peptoids (N-alkylglycine oligomers) we present a new synthetic methodology whereby N-heterocyclic carbene (NHC) based Pd ligands were assembled using a sub-monomer approach and loaded with Pd via solid-phase synthesis. This allowed the rapid generation a library of NHC–palladium catalysts that were readily functionalised to allow bioconjugation. These catalysts were able to rapidly activate a caged fluorophore and ‘switch-on’ an anticancer prodrug in 3D cell culture.

Graphical abstract: Solid-phase synthesis of biocompatible N-heterocyclic carbene–Pd catalysts using a sub-monomer approach

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Supplementary files

Article information


Submitted
28 Mar 2019
Accepted
06 May 2019
First published
08 May 2019

This article is Open Access

Org. Biomol. Chem., 2019,17, 5533-5537
Article type
Paper

Solid-phase synthesis of biocompatible N-heterocyclic carbene–Pd catalysts using a sub-monomer approach

D. Cherukaraveedu, P. T. Cowling, G. P. Birch, M. Bradley and A. Lilienkampf, Org. Biomol. Chem., 2019, 17, 5533
DOI: 10.1039/C9OB00716D

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