NHC/Phosphite Nickel(II) Precatalysts for the C–N Cross-Coupling of (Hetero)Aryl Chlorides under Mild Conditions
We report the synthesis of three nickel complexes based on Ni(NHC)[P(OR)<sub>3</sub>](Ar)Cl and their application in C(<i>sp</i><sup>2</sup>)-N cross-coupling reactions. Reactions involving secondary amines proceeded at room temperature, while anilines and primary alkyl amines coupled under mild heating. The reported complexes are air-stable as solids, operate at low catalytic loading, and do not require an exogenous ligand. Mechanistic studies suggest both free and Ni-bound phosphite are present during the reaction and that an isolated [Ni(NHC)(amine)(Ar)Cl] complex could be an on-cycle, catalytically active species.
Authors
- George A. Koutsantonis (ORCID: https://orcid.org/0000-0001-8755-3596)
- Stephen A. Moggach (ORCID: https://orcid.org/0000-0001-5339-7070)
- Reto Dorta (ORCID: https://orcid.org/0000-0003-1240-2755)
- Morgan John (ORCID: https://orcid.org/0009-0002-2814-8667)
- Dinesh N. Sawant (ORCID: https://orcid.org/0000-0003-2064-1692)
- Scott G. Stewart (ORCID: https://orcid.org/0000-0002-7537-247X)
- Nutan Rajendra Darandale (ORCID: https://orcid.org/0009-0005-0558-4417)
Institutions
- The University of Western Australia (AU)
- National Chemical Laboratory (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-09-09
- DOI
- https://doi.org/10.1021/acs.orglett.5c03230
- Citations
- 1
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94