Continuous Flow Synthesis of Metal–NHC Complexes

The use of weak bases and mild conditions is currently the most sustainable and attractive synthetic approach for the preparation of late‐transition metal complexes, some of which are widely used in catalysis, medicinal chemistry and materials science. Herein, the use of cuprate, aurate or palladate...

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Bibliographic Details
Published in:Chemistry : a European journal 2021-03, Vol.27 (18), p.5653-5657
Main Authors: Simoens, Andreas, Scattolin, Thomas, Cauwenbergh, Thibault, Pisanò, Gianmarco, Cazin, Catherine S. J., Stevens, Christian V., Nolan, Steven P.
Format: Article
Language:English
Subjects:
Acetone
Catalysis
Chemistry
Continuous flow
Coordination compounds
Copper
flow continuous synthesis
green solvents
Materials science
Metal complexes
N-heterocyclic carbene ligands
Synthesis
Transition metal compounds
weak-base route
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Summary:The use of weak bases and mild conditions is currently the most sustainable and attractive synthetic approach for the preparation of late‐transition metal complexes, some of which are widely used in catalysis, medicinal chemistry and materials science. Herein, the use of cuprate, aurate or palladate species for a continuous flow preparation of CuI, AuI and PdII‐NHC complexes is reported. All reactions examined proceed under extremely mild conditions and make use of technical grade acetone as solvent. The scalability of the process was exemplified in a multigram‐scale synthesis of [Cu(IPr)Cl]. Simplicity is the ultimate sophistication: Taking advantage of the mechanistic understanding of the weak base route to access metal–NHC complexes, the first continuous flow syntheses of CuI‐, AuI‐ and PdII‐NHC complexes using very mild conditions (40 °C, 2 min in technical grade acetone) are described.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202100190