Merging Electrolysis and Nickel Catalysis in Redox Neutral Cross-Coupling Reactions: Experiment and Computation for Electrochemically Induced C–P and C–Se Bonds Formation

Chen Zhu; Huifeng Yue; Pavlo Nikolaienko; Magnus Rueping

doi:10.31635/ccschem.020.201900112

Merging Electrolysis and Nickel Catalysis in Redox Neutral Cross-Coupling Reactions: Experiment and Computation for Electrochemically Induced C–P and C–Se Bonds Formation

Chen Zhu, Huifeng Yue, Pavlo Nikolaienko, Magnus Rueping

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

61 Scopus citations

Abstract

We have achieved a nickel-catalyzed cross-coupling reaction via concerted paired electrolysis under mild reaction conditions. In this electrochemical transformation, the anodic oxidation of Ni II to Ni III and cathodic reduction of Ni I to Ni 0 occurred simultaneously, resulting in an economical and sustainable cross-coupling protocol. Moreover, we performed mechanistic investigations, achieved by experiments and density functional theory (DFT) calculations for different C–heteroatom bond formations to reveal the catalytic cycle in more detail.

Original language	English (US)
Pages (from-to)	179-190
Number of pages	12
Journal	CCS Chemistry
DOIs	https://doi.org/10.31635/ccschem.020.201900112
State	Published - Mar 26 2020

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: C.Z. acknowledges King Abdullah University of Science and Technology (KAUST) for support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II. This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/3754).

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10.31635/ccschem.020.201900112

https://repository.kaust.edu.sa/bitstream/10754/662398/1/merging%20electrolysis.pdf

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title = "Merging Electrolysis and Nickel Catalysis in Redox Neutral Cross-Coupling Reactions: Experiment and Computation for Electrochemically Induced C–P and C–Se Bonds Formation",

abstract = "We have achieved a nickel-catalyzed cross-coupling reaction via concerted paired electrolysis under mild reaction conditions. In this electrochemical transformation, the anodic oxidation of Ni II to Ni III and cathodic reduction of Ni I to Ni 0 occurred simultaneously, resulting in an economical and sustainable cross-coupling protocol. Moreover, we performed mechanistic investigations, achieved by experiments and density functional theory (DFT) calculations for different C–heteroatom bond formations to reveal the catalytic cycle in more detail.",

author = "Chen Zhu and Huifeng Yue and Pavlo Nikolaienko and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: C.Z. acknowledges King Abdullah University of Science and Technology (KAUST) for support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II. This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/3754).",

year = "2020",

month = mar,

day = "26",

doi = "10.31635/ccschem.020.201900112",

language = "English (US)",

pages = "179--190",

journal = "CCS Chemistry",

issn = "2096-5745",

publisher = "Chinese Chemical Society",

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T1 - Merging Electrolysis and Nickel Catalysis in Redox Neutral Cross-Coupling Reactions: Experiment and Computation for Electrochemically Induced C–P and C–Se Bonds Formation

AU - Zhu, Chen

AU - Yue, Huifeng

AU - Nikolaienko, Pavlo

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: C.Z. acknowledges King Abdullah University of Science and Technology (KAUST) for support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II. This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/3754).

PY - 2020/3/26

Y1 - 2020/3/26

N2 - We have achieved a nickel-catalyzed cross-coupling reaction via concerted paired electrolysis under mild reaction conditions. In this electrochemical transformation, the anodic oxidation of Ni II to Ni III and cathodic reduction of Ni I to Ni 0 occurred simultaneously, resulting in an economical and sustainable cross-coupling protocol. Moreover, we performed mechanistic investigations, achieved by experiments and density functional theory (DFT) calculations for different C–heteroatom bond formations to reveal the catalytic cycle in more detail.

AB - We have achieved a nickel-catalyzed cross-coupling reaction via concerted paired electrolysis under mild reaction conditions. In this electrochemical transformation, the anodic oxidation of Ni II to Ni III and cathodic reduction of Ni I to Ni 0 occurred simultaneously, resulting in an economical and sustainable cross-coupling protocol. Moreover, we performed mechanistic investigations, achieved by experiments and density functional theory (DFT) calculations for different C–heteroatom bond formations to reveal the catalytic cycle in more detail.

UR - http://hdl.handle.net/10754/662398

UR - http://www.chinesechemsoc.org/doi/10.31635/ccschem.020.201900112

U2 - 10.31635/ccschem.020.201900112

DO - 10.31635/ccschem.020.201900112

M3 - Article

SN - 2096-5745

SP - 179

EP - 190

JO - CCS Chemistry

JF - CCS Chemistry

ER -

Merging Electrolysis and Nickel Catalysis in Redox Neutral Cross-Coupling Reactions: Experiment and Computation for Electrochemically Induced C–P and C–Se Bonds Formation

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