Dueker, Jonas and Philipp, Maximilian and Lentner, Thomas and Cadge, Jamie A. and Lavarda, Joao E. A. and Gschwind, Ruth M. and Sigman, Matthew S. and Ghosh, Indrajit and Koenig, Burkhard (2024) Cross-Coupling Reactions with Nickel, Visible Light, and tert-Butylamine as a Bifunctional Additive. ACS CATALYSIS, 15 (2). pp. 817-827. ISSN 2155-5435,
Full text not available from this repository. (Request a copy)Abstract
Transition metal catalysis is crucial for the synthesis of complex molecules, with ligands and bases playing a pivotal role in optimizing cross-coupling reactions. Despite advancements in ligand design and base selection, achieving effective synergy between these components remains challenging. We present here a general approach to nickel-catalyzed photoredox reactions employing tert-butylamine as a cost-effective bifunctional additive, acting as the base and ligand. This method proves effective for C-O and C-N bond-forming reactions with a diverse array of nucleophiles, including phenols, aliphatic alcohols, anilines, sulfonamides, sulfoximines, and imines. Notably, the protocol demonstrates significant applicability in biomolecule derivatization and facilitates sequential one-pot functionalizations. Spectroscopic investigations revealed the robustness of the dynamic catalytic system, while elucidation of structure-reactivity relationships demonstrated how computed molecular properties of both the nucleophile and electrophile correlated to reaction performance, providing a foundation for effective reaction outcome prediction.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CATALYZED C-N; BUCHWALD-HARTWIG AMINATION; BOND FORMATION; ARYL HALIDES; PHOTOREDOX; BASE; ARYLATION; ILLUMINATION; CHEMISTRY; ENABLES; AD-HoC; photoredox catalysis; visible light; nickel; cross-coupling; difunctionalization |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 07 Oct 2025 08:58 |
| Last Modified: | 07 Oct 2025 08:58 |
| URI: | https://pred.uni-regensburg.de/id/eprint/64335 |
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