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Cu(OTf)2‐mediated cross‐coupling of nitriles and N‐heterocycles with arylboronic acids to generate nitrilium and pyridinium products
- Publication Year :
- 2021
- Publisher :
- Wiley, 2021.
-
Abstract
- Metal-catalyzed C–N cross-coupling generally forms C−N bonds by reductive elimination from metal complexes bearing covalent C- and N-ligands. We have identified a Cu-mediated C–N cross-coupling that uses a dative N-ligand in the bond-forming event, which, in contrast to conventional methods, generates reactive cationic products. Mechanistic studies suggest the process operates via transmetalation of an aryl organoboron to a CuII complex bearing neutral N-ligands, such as nitriles or N-heterocycles. Subsequent generation of a putative CuIII complex enables the oxidative C–N coupling to take place, delivering nitrilium intermediates and pyridinium products. The reaction is general for a range of N(sp) and N(sp2) precursors and can be applied to drug synthesis and late-stage N-arylation, and the limitations in the methodology are mechanistically evidenced.
Details
- Language :
- English
- ISSN :
- 14337851
- Database :
- OpenAIRE
- Accession number :
- edsair.core.ac.uk....4bd2eac1981788931bb703f3b6eb54ca