Copper(i) complexes bearing mesoionic carbene ligands: influencing the activity in catalytic halo-click reactions. Issue 43 (3rd November 2020)

• Record Type: Journal Article
• Authors: Suntrup, Lisa; Beerhues, Julia; Etzold, Oliver; Sarkar, Biprajit
• Is Part Of: Dalton transactions. Volume 49:Issue 43(2020)
• Page Start: 15504
• Page End: 15510
• Publication Date: 2020-11-03
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/d0dt02023k
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : A series of mono- and dicopper complexes with mesoionic carbenes are tested as pre-catalysts for the halo-click reaction. Abstract : Metal complexes of mesoionic carbene (MIC) ligands are known to catalyze a variety of chemical transformations. In this contribution, we report on the synthesis of a dicationic dicopper(i ) complex containing a di-MIC ligand. Two routes are presented for the synthesis of the dicopper complex: Ag-mediated transmetalation and direct deprotonation. For the Ag-mediated transmetalation route, the detection and isolation of several Ag-containing intermediates that are relevant for the final formation of the aforementioned dicopper complex are reported. We then investigate a series of copper(i ) complexes based on MIC ligands as precatalysts for the azide halo-alkyne (Click) cycloaddition reaction. In a comparative study, three different halide-containing (I, Br, Cl) substrates have been investigated with different catalysts to survey the behaviour for mono/di-copper-MIC complexes as well as neutral, mono- and di-cationic complexes. The cationic complexes proved to have superior activities compared to the neutral species. These are the first reports on the use of Cu-MIC complexes as precatalysts for the halo-Click reaction.