Radical coupling of aryl halides to arenes facilitated by Ni(COD)(DQ) and other nickel sources

Seb Tyerman; Craig M. Robertson; John A. Murphy

doi:10.1039/D3OB01745A

Radical coupling of aryl halides to arenes facilitated by Ni(COD)(DQ) and other nickel sources

Seb Tyerman, Craig M. Robertson, John A. Murphy

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

12 Downloads (Pure)

Abstract

The air-stable complex Ni(COD)(DQ) (COD = 1,5-cyclooctadiene, DQ = duroquinone) promotes the coupling of aryl halides to arenes in the presence of KOtBu. This complex has recently been shown to perform coupling reactions based on organonickel intermediates, but in this case the coupling reactions proceed via aryl radicals as shown by our newly developed assay for aryl radicals. Coupling with this nickel source is more efficient than with Ni(COD)₂, Ni(PPh₃)₄ and Ni(acac)₂, all of which we also show to operate through aryl radical pathways.

Original language	English
Pages (from-to)	1023-1026
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	22
Issue number	5
Early online date	23 Dec 2023
DOIs	https://doi.org/10.1039/D3OB01745A
Publication status	Published - 7 Feb 2024

Funding

The authors thank GSK and EPSRC for funding an i-CASE studentship to ST (grant number EP/W522260/1). The authors thank Craig Irving, Patricia Keating, Jessica Bame and Graeme Anderson for assistance with spectroscopy.

Keywords

aryl halides
arenes
aryl radicals

Access to Document

10.1039/D3OB01745ALicence: CC BY 3.0

Tyerman-etal-OBC-2023-Radical-coupling-of-aryl-halides-to-arenesFinal published version, 669 KBLicence: CC BY 3.0

Industrial CASE Account - University of Strathclyde 2021 | Tyerman, Sebastian
Murphy, J. (Principal Investigator), Tuttle, T. (Co-investigator) & Tyerman, S. (Research Co-investigator)
EPSRC (Engineering and Physical Sciences Research Council)
1/10/21 → 1/10/25
Project: Research Studentship Case - Internally allocated

Cite this

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title = "Radical coupling of aryl halides to arenes facilitated by Ni(COD)(DQ) and other nickel sources",

abstract = "The air-stable complex Ni(COD)(DQ) (COD = 1,5-cyclooctadiene, DQ = duroquinone) promotes the coupling of aryl halides to arenes in the presence of KOtBu. This complex has recently been shown to perform coupling reactions based on organonickel intermediates, but in this case the coupling reactions proceed via aryl radicals as shown by our newly developed assay for aryl radicals. Coupling with this nickel source is more efficient than with Ni(COD)2, Ni(PPh3)4 and Ni(acac)2, all of which we also show to operate through aryl radical pathways.",

keywords = "aryl halides, arenes, aryl radicals",

author = "Seb Tyerman and Robertson, \{Craig M.\} and Murphy, \{John A.\}",

year = "2024",

month = feb,

day = "7",

doi = "10.1039/D3OB01745A",

language = "English",

volume = "22",

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journal = "Organic and Biomolecular Chemistry",

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publisher = "Royal Society of Chemistry",

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T1 - Radical coupling of aryl halides to arenes facilitated by Ni(COD)(DQ) and other nickel sources

AU - Tyerman, Seb

AU - Robertson, Craig M.

AU - Murphy, John A.

PY - 2024/2/7

Y1 - 2024/2/7

N2 - The air-stable complex Ni(COD)(DQ) (COD = 1,5-cyclooctadiene, DQ = duroquinone) promotes the coupling of aryl halides to arenes in the presence of KOtBu. This complex has recently been shown to perform coupling reactions based on organonickel intermediates, but in this case the coupling reactions proceed via aryl radicals as shown by our newly developed assay for aryl radicals. Coupling with this nickel source is more efficient than with Ni(COD)2, Ni(PPh3)4 and Ni(acac)2, all of which we also show to operate through aryl radical pathways.

AB - The air-stable complex Ni(COD)(DQ) (COD = 1,5-cyclooctadiene, DQ = duroquinone) promotes the coupling of aryl halides to arenes in the presence of KOtBu. This complex has recently been shown to perform coupling reactions based on organonickel intermediates, but in this case the coupling reactions proceed via aryl radicals as shown by our newly developed assay for aryl radicals. Coupling with this nickel source is more efficient than with Ni(COD)2, Ni(PPh3)4 and Ni(acac)2, all of which we also show to operate through aryl radical pathways.

KW - aryl halides

KW - arenes

KW - aryl radicals

U2 - 10.1039/D3OB01745A

DO - 10.1039/D3OB01745A

M3 - Article

SN - 1477-0520

VL - 22

SP - 1023

EP - 1026

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 5

ER -

Radical coupling of aryl halides to arenes facilitated by Ni(COD)(DQ) and other nickel sources

Abstract

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Keywords

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Industrial CASE Account - University of Strathclyde 2021 | Tyerman, Sebastian

Cite this