Rapid aqueous 'click chemistry' using Cu(I)-loaded dendrimers as macromolecular catalysts

Eli Moore; Steven J. McInnes; Andrew Vogt; Nicolas H. Voelcker

doi:10.1016/j.tetlet.2011.02.090

Rapid aqueous 'click chemistry' using Cu(I)-loaded dendrimers as macromolecular catalysts

Eli Moore, Steven J. McInnes, Andrew Vogt, Nicolas H. Voelcker

Research output: Contribution to journal › Article › Research › peer-review

21 Citations (Scopus)

Abstract

Here, we investigate the catalytic activity of various copper (Cu)-loaded poly(amido amine) (PAMAM) dendrimers towards the Cu(I)-catalysed azide-alkyne cycloaddition (CuAAC). Reactivity is tested on a model reaction between azido propanol and propargyl alcohol in aqueous solution. We observe significantly faster conversion using PAMAM dendrimers as macromolecular Cu(I) ligands compared to traditional small molecular ligand systems, and demonstrate that the macromolecular catalyst can be removed by ultrafiltration.

Original language	English
Pages (from-to)	2327-2329
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2011.02.090
Publication status	Published - 4 May 2011
Externally published	Yes

Keywords

Catalyst
Click chemistry
Dendrimer
PAMAM

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10.1016/j.tetlet.2011.02.090

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title = "Rapid aqueous 'click chemistry' using Cu(I)-loaded dendrimers as macromolecular catalysts",

abstract = "Here, we investigate the catalytic activity of various copper (Cu)-loaded poly(amido amine) (PAMAM) dendrimers towards the Cu(I)-catalysed azide-alkyne cycloaddition (CuAAC). Reactivity is tested on a model reaction between azido propanol and propargyl alcohol in aqueous solution. We observe significantly faster conversion using PAMAM dendrimers as macromolecular Cu(I) ligands compared to traditional small molecular ligand systems, and demonstrate that the macromolecular catalyst can be removed by ultrafiltration. ",

keywords = "Catalyst, Click chemistry, Dendrimer, PAMAM",

author = "Eli Moore and McInnes, {Steven J.} and Andrew Vogt and Voelcker, {Nicolas H.}",

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doi = "10.1016/j.tetlet.2011.02.090",

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T1 - Rapid aqueous 'click chemistry' using Cu(I)-loaded dendrimers as macromolecular catalysts

AU - Moore, Eli

AU - McInnes, Steven J.

AU - Vogt, Andrew

AU - Voelcker, Nicolas H.

PY - 2011/5/4

Y1 - 2011/5/4

N2 - Here, we investigate the catalytic activity of various copper (Cu)-loaded poly(amido amine) (PAMAM) dendrimers towards the Cu(I)-catalysed azide-alkyne cycloaddition (CuAAC). Reactivity is tested on a model reaction between azido propanol and propargyl alcohol in aqueous solution. We observe significantly faster conversion using PAMAM dendrimers as macromolecular Cu(I) ligands compared to traditional small molecular ligand systems, and demonstrate that the macromolecular catalyst can be removed by ultrafiltration.

AB - Here, we investigate the catalytic activity of various copper (Cu)-loaded poly(amido amine) (PAMAM) dendrimers towards the Cu(I)-catalysed azide-alkyne cycloaddition (CuAAC). Reactivity is tested on a model reaction between azido propanol and propargyl alcohol in aqueous solution. We observe significantly faster conversion using PAMAM dendrimers as macromolecular Cu(I) ligands compared to traditional small molecular ligand systems, and demonstrate that the macromolecular catalyst can be removed by ultrafiltration.

KW - Catalyst

KW - Click chemistry

KW - Dendrimer

KW - PAMAM

UR - http://www.scopus.com/inward/record.url?scp=79953292729&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2011.02.090

DO - 10.1016/j.tetlet.2011.02.090

M3 - Article

AN - SCOPUS:79953292729

VL - 52

SP - 2327

EP - 2329

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 18

ER -

Rapid aqueous 'click chemistry' using Cu(I)-loaded dendrimers as macromolecular catalysts

Abstract

Keywords

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