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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. und 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, S. 2367-2372.
Veröffentlichungsdatum dieses Volltextes: 08 Mai 2020 06:00
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.43140
Zusammenfassung
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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| Dokumentenart | Artikel | ||||
| Titel eines Journals oder einer Zeitschrift | Advanced Synthesis & Catalysis | ||||
| Verlag: | Wiley | ||||
|---|---|---|---|---|---|
| Ort der Veröffentlichung: | WEINHEIM | ||||
| Band: | 362 | ||||
| Seitenbereich: | S. 2367-2372 | ||||
| Datum | 2020 | ||||
| Institutionen | Chemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König | ||||
| Identifikationsnummer |
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| Stichwörter / 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-Dezimal-Klassifikation | 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status | Veröffentlicht | ||||
| Begutachtet | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden | Zum Teil | ||||
| URN der UB Regensburg | urn:nbn:de:bvb:355-epub-431404 | ||||
| Dokumenten-ID | 43140 |
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