Photoredox/Nickel Dual-Catalyzed Reductive Cross Coupling of Aryl Halides Using an Organic Reducing Agent

Abhishek Dewanji; Raoul F. Bülow; Magnus Rueping

doi:10.1021/acs.orglett.0c00199

Photoredox/Nickel Dual-Catalyzed Reductive Cross Coupling of Aryl Halides Using an Organic Reducing Agent

Abhishek Dewanji, Raoul F. Bülow, Magnus Rueping

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38 Scopus citations

Abstract

A successful protocol for the reductive aryl−aryl cross-coupling of polyfluorinated arenes with a broad range of aryl halides has been developed. Sequential carbon−fluorine bond cleavage and carbon−carbon bond formation are two of the important features of the reaction. Addition of an aryl radical anion to a nickel intermediate was achieved for the first time using polyfluoroarenes as radical precursors. This, in combination with the excellent para selectivity, paves the way for the synthesis of various new multifluorinated biaryl compounds.

Original language	English (US)
Pages (from-to)	1611-1617
Number of pages	7
Journal	Organic Letters
Volume	22
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.0c00199
State	Published - Feb 3 2020

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10.1021/acs.orglett.0c00199

https://repository.kaust.edu.sa/bitstream/10754/661439/1/Manuscript_accepted.pdf

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title = "Photoredox/Nickel Dual-Catalyzed Reductive Cross Coupling of Aryl Halides Using an Organic Reducing Agent",

abstract = "A successful protocol for the reductive aryl−aryl cross-coupling of polyfluorinated arenes with a broad range of aryl halides has been developed. Sequential carbon−fluorine bond cleavage and carbon−carbon bond formation are two of the important features of the reaction. Addition of an aryl radical anion to a nickel intermediate was achieved for the first time using polyfluoroarenes as radical precursors. This, in combination with the excellent para selectivity, paves the way for the synthesis of various new multifluorinated biaryl compounds.",

author = "Abhishek Dewanji and B{\"u}low, {Raoul F.} and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The research leading to these results has received funding from the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP/2007−2013)/ERC Grant Agreement No. 617044 (SunCatChem).",

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doi = "10.1021/acs.orglett.0c00199",

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T1 - Photoredox/Nickel Dual-Catalyzed Reductive Cross Coupling of Aryl Halides Using an Organic Reducing Agent

AU - Dewanji, Abhishek

AU - Bülow, Raoul F.

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The research leading to these results has received funding from the European Research Council under the European Union’s Seventh Framework Programme (FP/2007−2013)/ERC Grant Agreement No. 617044 (SunCatChem).

PY - 2020/2/3

Y1 - 2020/2/3

N2 - A successful protocol for the reductive aryl−aryl cross-coupling of polyfluorinated arenes with a broad range of aryl halides has been developed. Sequential carbon−fluorine bond cleavage and carbon−carbon bond formation are two of the important features of the reaction. Addition of an aryl radical anion to a nickel intermediate was achieved for the first time using polyfluoroarenes as radical precursors. This, in combination with the excellent para selectivity, paves the way for the synthesis of various new multifluorinated biaryl compounds.

AB - A successful protocol for the reductive aryl−aryl cross-coupling of polyfluorinated arenes with a broad range of aryl halides has been developed. Sequential carbon−fluorine bond cleavage and carbon−carbon bond formation are two of the important features of the reaction. Addition of an aryl radical anion to a nickel intermediate was achieved for the first time using polyfluoroarenes as radical precursors. This, in combination with the excellent para selectivity, paves the way for the synthesis of various new multifluorinated biaryl compounds.

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ER -

Photoredox/Nickel Dual-Catalyzed Reductive Cross Coupling of Aryl Halides Using an Organic Reducing Agent

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