Reactivity in Nickel Catalyzed Multicomponent Sequential Reductive Cross-Coupling Reactions

Haifeng Chen; Huifeng Yue; Chen Zhu; Magnus Rueping

doi:10.1002/anie.202204144

Reactivity in Nickel Catalyzed Multicomponent Sequential Reductive Cross-Coupling Reactions

Haifeng Chen, Huifeng Yue, Chen Zhu, Magnus Rueping

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

35 Scopus citations

Abstract

A nickel-catalyzed three-component reductive carbonylation of alkyl halides, aryl halides, and ethyl chloroformate is described. Ethyl chloroformate is utilized as a safe and readily available source of CO in this multi-component protocol, providing an efficient and practical alternative for the synthesis of aryl-alkyl ketones. The reaction exhibits a wide substrate scope and good functional group compatibility. Experimental and DFT mechanistic studies highlight the complexity the cross-electrophile coupling and provide insight into the sequence of the three consecutive oxidative additions of aryl halide, chloroformate and akyl halide.

Original language	English (US)
Journal	Angewandte Chemie International Edition
DOIs	https://doi.org/10.1002/anie.202204144
State	Published - Jun 21 2022

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.202204144

https://repository.kaust.edu.sa/bitstream/10754/679245/1/Angew%20Chem%20Int%20Ed%20-%202022%20-%20Chen%20-%20Reactivity%20in%20Nickel%20Catalyzed%20Multicomponent%20Sequential%20Reductive%20Cross%e2%80%90Coupling.pdf

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title = "Reactivity in Nickel Catalyzed Multicomponent Sequential Reductive Cross-Coupling Reactions",

abstract = "A nickel-catalyzed three-component reductive carbonylation of alkyl halides, aryl halides, and ethyl chloroformate is described. Ethyl chloroformate is utilized as a safe and readily available source of CO in this multi-component protocol, providing an efficient and practical alternative for the synthesis of aryl-alkyl ketones. The reaction exhibits a wide substrate scope and good functional group compatibility. Experimental and DFT mechanistic studies highlight the complexity the cross-electrophile coupling and provide insight into the sequence of the three consecutive oxidative additions of aryl halide, chloroformate and akyl halide.",

author = "Haifeng Chen and Huifeng Yue and Chen Zhu and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2022-06-23 Acknowledgements: The authors thank the King Abdullah University of Science and Technology (KAUST) for financial support and the KAUST Supercomputing Laboratory for providing the computational resources of the Shaheen II supercomputer.",

year = "2022",

month = jun,

day = "21",

doi = "10.1002/anie.202204144",

language = "English (US)",

journal = "Angewandte Chemie International Edition",

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publisher = "John Wiley and Sons Ltd",

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T1 - Reactivity in Nickel Catalyzed Multicomponent Sequential Reductive Cross-Coupling Reactions

AU - Chen, Haifeng

AU - Yue, Huifeng

AU - Zhu, Chen

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2022-06-23 Acknowledgements: The authors thank the King Abdullah University of Science and Technology (KAUST) for financial support and the KAUST Supercomputing Laboratory for providing the computational resources of the Shaheen II supercomputer.

PY - 2022/6/21

Y1 - 2022/6/21

N2 - A nickel-catalyzed three-component reductive carbonylation of alkyl halides, aryl halides, and ethyl chloroformate is described. Ethyl chloroformate is utilized as a safe and readily available source of CO in this multi-component protocol, providing an efficient and practical alternative for the synthesis of aryl-alkyl ketones. The reaction exhibits a wide substrate scope and good functional group compatibility. Experimental and DFT mechanistic studies highlight the complexity the cross-electrophile coupling and provide insight into the sequence of the three consecutive oxidative additions of aryl halide, chloroformate and akyl halide.

AB - A nickel-catalyzed three-component reductive carbonylation of alkyl halides, aryl halides, and ethyl chloroformate is described. Ethyl chloroformate is utilized as a safe and readily available source of CO in this multi-component protocol, providing an efficient and practical alternative for the synthesis of aryl-alkyl ketones. The reaction exhibits a wide substrate scope and good functional group compatibility. Experimental and DFT mechanistic studies highlight the complexity the cross-electrophile coupling and provide insight into the sequence of the three consecutive oxidative additions of aryl halide, chloroformate and akyl halide.

UR - http://hdl.handle.net/10754/679245

UR - https://onlinelibrary.wiley.com/doi/10.1002/anie.202204144

U2 - 10.1002/anie.202204144

DO - 10.1002/anie.202204144

M3 - Article

C2 - 35727897

SN - 1433-7851

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

ER -

Reactivity in Nickel Catalyzed Multicomponent Sequential Reductive Cross-Coupling Reactions

Abstract

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