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

Catalysis Research Center

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

35 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 1 2011

Keywords

Acylation
Homogeneous catalysis
Immobilization
Organocatalysis
Supported catalysis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/ejoc.201001507

Cite this

@article{0feff1f717e442bcacf14913e44fc189,

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 = "{D Elia}, Valerio and Yinghao Liu and Hendrik Zipse",

year = "2011",

month = mar,

day = "1",

doi = "10.1002/ejoc.201001507",

language = "English (US)",

pages = "1527--1533",

journal = "Justus Liebigs Annalen der Chemie",

issn = "0075-4617",

publisher = "Wiley-VCH Verlag",

number = "8",

}

TY - JOUR

T1 - Immobilized DMAP derivatives rivaling homogeneous DMAP

AU - D Elia, Valerio

AU - Liu, Yinghao

AU - Zipse, Hendrik

PY - 2011/3/1

Y1 - 2011/3/1

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

UR - http://www.scopus.com/inward/record.url?scp=79952150587&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201001507

DO - 10.1002/ejoc.201001507

M3 - Article

AN - SCOPUS:79952150587

SN - 0075-4617

SP - 1527

EP - 1533

JO - Justus Liebigs Annalen der Chemie

JF - Justus Liebigs Annalen der Chemie

IS - 8

ER -

Immobilized DMAP derivatives rivaling homogeneous DMAP

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this