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C(sp3)−C(sp3) Cross‐Coupling of Alkyl Bromides and Ethers Mediated by Metal and Visible Light Photoredox Catalysis
Santos, Marilia S.
, Corrêa, Arlene G.
, Paixão, Márcio W. and König, Burkhard
(2020)
C(sp3)−C(sp3) Cross‐Coupling of Alkyl Bromides and Ethers Mediated by Metal and Visible Light Photoredox Catalysis.
Advanced Synthesis & Catalysis 362, pp. 2367-2372.
Date of publication of this fulltext: 08 May 2020 06:00
Article
DOI to cite this document: 10.5283/epub.43140
Abstract
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 ...
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.
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| Item type | Article | ||||
| Journal or Publication Title | Advanced Synthesis & Catalysis | ||||
| Publisher: | Wiley | ||||
|---|---|---|---|---|---|
| Place of Publication: | WEINHEIM | ||||
| Volume: | 362 | ||||
| Page Range: | pp. 2367-2372 | ||||
| Date | 2020 | ||||
| Institutions | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König | ||||
| Identification Number |
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| Keywords | C-H FUNCTIONALIZATION; HYDROGEN-ATOM TRANSFER; CARBON BOND FORMATION; HALIDES; PHOTOCATALYSIS; REAGENTS; ARYL; cross-coupling; alkyl bromides; dual catalysis; visible-light; nickel; ethers | ||||
| Dewey Decimal Classification | 500 Science > 540 Chemistry & allied sciences | ||||
| Status | Published | ||||
| Refereed | Yes, this version has been refereed | ||||
| Created at the University of Regensburg | Partially | ||||
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-431404 | ||||
| Item ID | 43140 |
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