Dinuclear thiazolylidene copper complex as highly active catalyst for azid-alkyne cycloadditions

A dinuclear N-heterocyclic carbene (NHC) copper complex efficiently catalyzes azide-alkyne cycloaddition (CuAAC) "click" reactions. The ancillary ligand comprises two 4,5-dimethyl-1,3-thiazol-2-ylidene units and an ethylene linker. The three-step preparation of the complex from commerciall...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2016-07, Vol.12 (1), p.1566-1572
Main Authors: Schöffler, Anne L, Makarem, Ata, Rominger, Frank, Straub, Bernd F
Format: Article
Language:English
Subjects:
catalysis
Chemistry
click
copper
CuAAC
Full Research Paper
N-heterocyclic carbene
thiazole
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Summary:A dinuclear N-heterocyclic carbene (NHC) copper complex efficiently catalyzes azide-alkyne cycloaddition (CuAAC) "click" reactions. The ancillary ligand comprises two 4,5-dimethyl-1,3-thiazol-2-ylidene units and an ethylene linker. The three-step preparation of the complex from commercially available starting compounds is more straightforward and cost-efficient than that of the previously described 1,2,4-triazol-5-ylidene derivatives. Kinetic experiments revealed its high catalytic CuAAC activity in organic solvents at room temperature. The activity increases upon addition of acetic acid, particularly for more acidic alkyne substrates. The modular catalyst design renders possible the exchange of N-heterocyclic carbene, linker, sacrificial ligand, and counter ion.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.12.151