Abstract
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.
Highlights
The copper-catalyzed azide–alkyne cycloaddition (CuAAC) is one of the most important “click” reactions for the facile covalent linking of two molecules [1,2,3]
We report the synthesis of an ethylene-linked bisthiazol2-ylidene dicopper(I) complex 2 that features high catalytic activity in CuAAC reactions
The similarity of NMRspectroscopic data of the 1,2,4-triazol-5-ylidene and the 1,3thiazol-2-ylidene dicopper complex indicate that the complexes of both N-heterocyclic carbene (NHC) ligand types consist of a bis-NHC ligand, two copper(I) ions and a labile acetate ligand that bridges the metal centers
Summary
The copper-catalyzed azide–alkyne cycloaddition (CuAAC) is one of the most important “click” reactions for the facile covalent linking of two molecules [1,2,3]. We report the synthesis of an ethylene-linked bisthiazol2-ylidene dicopper(I) complex 2 that features high catalytic activity in CuAAC reactions.
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