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Santos, Marilia S. ; Corrêa, Arlene G. ; Paixão, Márcio W. ; König, Burkhard

C(sp3)−C(sp3) Cross‐Coupling of Alkyl Bromides and Ethers Mediated by Metal and Visible Light Photoredox Catalysis

Article

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.

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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Details

Item typeArticle
Journal or Publication TitleAdvanced Synthesis & Catalysis
PublisherWiley
Open Access TypeDEAL (Wiley)
Place of PublicationWEINHEIM
Volume362
Page Rangepp. 2367-2372
Date2020
Date of publication08 May 2020 06:00
InstitutionsChemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Identification Number
ValueType
10.1002/adsc.202000167DOI
KeywordsC-H FUNCTIONALIZATION; HYDROGEN-ATOM TRANSFER; CARBON BOND FORMATION; HALIDES; PHOTOCATALYSIS; REAGENTS; ARYL; cross-coupling; alkyl bromides; dual catalysis; visible-light; nickel; ethers
Dewey Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgPartially
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-431404
Item ID43140

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