Functionalized Organocatalytic Nanoreactors: Hydrophobic Pockets for Acylation Reactions in Water

Pepa Cotanda; Annhelen Lu; Joseph P. Patterson; Nikos Petzetakis; Rachel K. O'Reilly

doi:10.1021/ma2027462

Functionalized Organocatalytic Nanoreactors: Hydrophobic Pockets for Acylation Reactions in Water

Pepa Cotanda, Annhelen Lu, Joseph P. Patterson, Nikos Petzetakis, Rachel K. O'Reilly

Chemistry

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

84 Citations (Scopus)

Abstract

The effect of covalently attaching 4-(dimethylamino)pyridine (DMAP) functionality to the hydrophobic core of a polymeric micelle in water has been investigated in the context of acylation reactions employing non-water-soluble substrates. For this purpose a novel temperature-responsive polymeric micelle has been synthesized using reversible addition–fragmentation chain transfer (RAFT) polymerization techniques. The reactivity of the tethered organocatalyst within the nanostructure was found to be extremely high, improving in some cases the acylation rates up to 100 times compared to those for unsupported DMAP in organic solvents. Moreover, the catalytic nanoreactors have been demonstrated to be capable of reuse up to 6 times while maintaining high activity.

Original language	English
Pages (from-to)	2377-2384
Journal	Macromolecules
Volume	45
Issue number	5
DOIs	https://doi.org/10.1021/ma2027462
Publication status	Published - 29 Feb 2012

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AU - O'Reilly, Rachel K.

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AB - The effect of covalently attaching 4-(dimethylamino)pyridine (DMAP) functionality to the hydrophobic core of a polymeric micelle in water has been investigated in the context of acylation reactions employing non-water-soluble substrates. For this purpose a novel temperature-responsive polymeric micelle has been synthesized using reversible addition–fragmentation chain transfer (RAFT) polymerization techniques. The reactivity of the tethered organocatalyst within the nanostructure was found to be extremely high, improving in some cases the acylation rates up to 100 times compared to those for unsupported DMAP in organic solvents. Moreover, the catalytic nanoreactors have been demonstrated to be capable of reuse up to 6 times while maintaining high activity.

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Functionalized Organocatalytic Nanoreactors: Hydrophobic Pockets for Acylation Reactions in Water

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