Santos, Marilia S. and Correa, Arlene G. and Paixao, Marcio W. and Koenig, Burkhard (2020) C(sp(3))-C(sp(3)) Cross-Coupling of Alkyl Bromides and Ethers Mediated by Metal and Visible Light Photoredox Catalysis. ADVANCED SYNTHESIS & CATALYSIS, 362 (12). pp. 2367-2372. ISSN 1615-4150, 1615-4169
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We report a C(sp(3))-C(sp(3)) cross-coupling of alkyl bromides and alkyl chlorides with ethers by dual photoredox-nickel catalysis. The catalytic system comprises of the organic photocatalyst 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4-CzIPN) and bench stable nickel (II) acetylacetonate in the presence of visible-light, providing the coupling products in up to 92% yield. Preliminary mechanistic studies suggest two catalytic cycles, as well as the photogeneration of bromine or chlorine radicals from halide atoms that are present in the structures of the coupling partners. The halide radical mediates the hydrogen atom transfer event, avoiding the need of an additional HAT catalyst.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | C-H FUNCTIONALIZATION; HYDROGEN-ATOM TRANSFER; CARBON BOND FORMATION; HALIDES; PHOTOCATALYSIS; REAGENTS; ARYL; cross-coupling; alkyl bromides; dual catalysis; visible-light; nickel; ethers |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 26 Mar 2021 11:17 |
| Last Modified: | 26 Mar 2021 11:17 |
| URI: | https://pred.uni-regensburg.de/id/eprint/44698 |
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