Immobilized DMAP derivatives rivaling homogeneous DMAP

Valerio D'Elia; Yinghao Liu; Hendrik Zipse

doi:10.1002/ejoc.201001507

Immobilized DMAP derivatives rivaling homogeneous DMAP

Valerio D'Elia, Yinghao Liu, Hendrik Zipse^*

^*Corresponding author for this work

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

43 Scopus citations

Abstract

The copper-catalyzed Huisgen reaction between azides and alkynes was utilized to covalently attach derivatives of 4-(dimethylamino)pyridine (DMAP) to a polystyrene resin (PS) support. The catalytic potential of these constructs as determined in acylation and aza-Morita-Baylis-Hillman reactions far exceeds that of commercially available DMAP-PS resins and is fully competitive with DMAP in homogeneous solution. Immobilization of 3,4-diaminopyridine catalysts on polystyrene by using the copper-catalyzed Huisgen reaction allowed the preparation of new supported catalysts ofunprecedented catalytic activity in acylation and aza-Morita-Baylis-Hillman reactions.

Original language	English (US)
Pages (from-to)	1527-1533
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	8
DOIs	https://doi.org/10.1002/ejoc.201001507
State	Published - Mar 2011

Keywords

Acylation
Homogeneous catalysis
Immobilization
Organocatalysis
Supported catalysis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201001507

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title = "Immobilized DMAP derivatives rivaling homogeneous DMAP",

abstract = "The copper-catalyzed Huisgen reaction between azides and alkynes was utilized to covalently attach derivatives of 4-(dimethylamino)pyridine (DMAP) to a polystyrene resin (PS) support. The catalytic potential of these constructs as determined in acylation and aza-Morita-Baylis-Hillman reactions far exceeds that of commercially available DMAP-PS resins and is fully competitive with DMAP in homogeneous solution. Immobilization of 3,4-diaminopyridine catalysts on polystyrene by using the copper-catalyzed Huisgen reaction allowed the preparation of new supported catalysts ofunprecedented catalytic activity in acylation and aza-Morita-Baylis-Hillman reactions.",

keywords = "Acylation, Homogeneous catalysis, Immobilization, Organocatalysis, Supported catalysis",

author = "Valerio D'Elia and Yinghao Liu and Hendrik Zipse",

year = "2011",

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pages = "1527--1533",

journal = "European Journal of Organic Chemistry",

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T1 - Immobilized DMAP derivatives rivaling homogeneous DMAP

AU - D'Elia, Valerio

AU - Liu, Yinghao

AU - Zipse, Hendrik

PY - 2011/3

Y1 - 2011/3

N2 - The copper-catalyzed Huisgen reaction between azides and alkynes was utilized to covalently attach derivatives of 4-(dimethylamino)pyridine (DMAP) to a polystyrene resin (PS) support. The catalytic potential of these constructs as determined in acylation and aza-Morita-Baylis-Hillman reactions far exceeds that of commercially available DMAP-PS resins and is fully competitive with DMAP in homogeneous solution. Immobilization of 3,4-diaminopyridine catalysts on polystyrene by using the copper-catalyzed Huisgen reaction allowed the preparation of new supported catalysts ofunprecedented catalytic activity in acylation and aza-Morita-Baylis-Hillman reactions.

AB - The copper-catalyzed Huisgen reaction between azides and alkynes was utilized to covalently attach derivatives of 4-(dimethylamino)pyridine (DMAP) to a polystyrene resin (PS) support. The catalytic potential of these constructs as determined in acylation and aza-Morita-Baylis-Hillman reactions far exceeds that of commercially available DMAP-PS resins and is fully competitive with DMAP in homogeneous solution. Immobilization of 3,4-diaminopyridine catalysts on polystyrene by using the copper-catalyzed Huisgen reaction allowed the preparation of new supported catalysts ofunprecedented catalytic activity in acylation and aza-Morita-Baylis-Hillman reactions.

KW - Acylation

KW - Homogeneous catalysis

KW - Immobilization

KW - Organocatalysis

KW - Supported catalysis

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DO - 10.1002/ejoc.201001507

M3 - Article

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SN - 1434-193X

SP - 1527

EP - 1533

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 8

ER -

Immobilized DMAP derivatives rivaling homogeneous DMAP

Abstract

Keywords

ASJC Scopus subject areas

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