Nickel catalyzed C-N coupling of haloarenes with B<sub>2</sub>N<sub>4</sub> reagents.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 40180918.
- Also identified by DOI 10.1038/s41467-025-58438-6 and PMC identifier 11968942.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
Abstract
Carbon-heteroatom bond (especially for C-N bond) formation through nickel catalysis has seen significant development. Well-established Ni(0)/Ni(II) redox cycle and photoinduced Ni(I)/Ni(III) redox cycle have been the dominant mechanisms. We report a thermally driven Ni-catalyzed method for C-N bond formation between haloarenes and B<sub>2</sub>N<sub>4</sub> reagents, yielding N,N-dialkylaniline derivatives in good to excellent yields with broad functional group tolerance under base-free conditions. The catalytic protocol is useful for base-sensitive structures and late-stage modifications of complex molecules. Detailed mechanistic studies and density functional theory (DFT) calculations indicate that a Ni(I)/Ni(III) redox cycle is preferred in the C-N coupling process, and B<sub>2</sub>N<sub>4</sub> reagent serves both as a single electron transfer donor and a N,N-dialkylation source.