Immobilized DMAP Derivatives Rivaling Homogeneous DMAP

• Published in: European Journal of Organic Chemistry Vol. 2011; no. 8; pp. 1527 - 1533
• Main Authors: D'Elia, Valerio, Liu, Yinghao, Zipse, Hendrik
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01-03-2011; WILEY‐VCH Verlag; Wiley-VCH
• Subjects: Acylation; Catalysis; Catalysts: preparations and properties; Chemistry; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Homogeneous catalysis; Immobilization; Organic chemistry; Organocatalysis; Preparations and properties; Supported catalysis; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Chemical solution; Catalytic reaction; Acetylenic compound; Organic azide; Nitrogen heterocycle; Immobilization; Transition metal; Supported catalysis; Organocatalysis; Supported catalyst; Huisgen cycloaddition; Pyridine derivatives; Styrene derivative polymer; Azides; Copper ion; Homogeneous catalysis; Baylis-Hillman reaction; Acylation; Alkyne
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201001507

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.