Metal Cations from Sacrificial Anodes Act as a Lewis Acid Co-Catalyst in Electrochemical Cross-Coupling of Aryl Bromides and Aziridines

Gadde Sathish Kumar; Chen Zhu; Rajesh Kancherla; Prashant S. Shinde; Magnus Rueping

doi:10.1021/acscatal.3c01503

Metal Cations from Sacrificial Anodes Act as a Lewis Acid Co-Catalyst in Electrochemical Cross-Coupling of Aryl Bromides and Aziridines

Gadde Sathish Kumar, Chen Zhu, Rajesh Kancherla, Prashant S. Shinde, Magnus Rueping^*

^*Corresponding author for this work

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

19 Scopus citations

Abstract

An efficient method for the reductive cross-electrophile coupling of aziridines with aryl halides using nickel electrocatalysis is reported. This reaction provides valuable phenethylamines at room temperature in good yields. The reaction was successfully applied to the electro-reductive cross-coupling of less reactive, unsubstituted N-tosylaziridine. Additionally, we were even able to couple challenging alkyl bromides with aryl aziridines. Control experiments and voltammetric studies confirm that the mechanism is distinct from conventional and photochemical couplings. Furthermore, the role of both Ni(II) organometallic complexes and electrodes was examined, providing insight into the reaction mechanism and the beneficial role of the sacrificial anode in electrochemical cross-couplings.

Original language	English (US)
Pages (from-to)	8813-8820
Number of pages	8
Journal	ACS Catalysis
Volume	13
Issue number	13
DOIs	https://doi.org/10.1021/acscatal.3c01503
State	Published - Jul 7 2023

Bibliographical note

Funding Information:
This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4405). The authors acknowledge KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.

Publisher Copyright:
© 2023 American Chemical Society

Keywords

aziridine
cross-coupling
electrochemical
iron
Lewis acid
nickel

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1021/acscatal.3c01503

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title = "Metal Cations from Sacrificial Anodes Act as a Lewis Acid Co-Catalyst in Electrochemical Cross-Coupling of Aryl Bromides and Aziridines",

abstract = "An efficient method for the reductive cross-electrophile coupling of aziridines with aryl halides using nickel electrocatalysis is reported. This reaction provides valuable phenethylamines at room temperature in good yields. The reaction was successfully applied to the electro-reductive cross-coupling of less reactive, unsubstituted N-tosylaziridine. Additionally, we were even able to couple challenging alkyl bromides with aryl aziridines. Control experiments and voltammetric studies confirm that the mechanism is distinct from conventional and photochemical couplings. Furthermore, the role of both Ni(II) organometallic complexes and electrodes was examined, providing insight into the reaction mechanism and the beneficial role of the sacrificial anode in electrochemical cross-couplings.",

keywords = "aziridine, cross-coupling, electrochemical, iron, Lewis acid, nickel",

author = "Kumar, {Gadde Sathish} and Chen Zhu and Rajesh Kancherla and Shinde, {Prashant S.} and Magnus Rueping",

note = "Funding Information: This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4405). The authors acknowledge KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II. Publisher Copyright: {\textcopyright} 2023 American Chemical Society",

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doi = "10.1021/acscatal.3c01503",

language = "English (US)",

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AU - Kumar, Gadde Sathish

AU - Zhu, Chen

AU - Kancherla, Rajesh

AU - Shinde, Prashant S.

AU - Rueping, Magnus

N1 - Funding Information: This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4405). The authors acknowledge KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II. Publisher Copyright: © 2023 American Chemical Society

PY - 2023/7/7

Y1 - 2023/7/7

N2 - An efficient method for the reductive cross-electrophile coupling of aziridines with aryl halides using nickel electrocatalysis is reported. This reaction provides valuable phenethylamines at room temperature in good yields. The reaction was successfully applied to the electro-reductive cross-coupling of less reactive, unsubstituted N-tosylaziridine. Additionally, we were even able to couple challenging alkyl bromides with aryl aziridines. Control experiments and voltammetric studies confirm that the mechanism is distinct from conventional and photochemical couplings. Furthermore, the role of both Ni(II) organometallic complexes and electrodes was examined, providing insight into the reaction mechanism and the beneficial role of the sacrificial anode in electrochemical cross-couplings.

AB - An efficient method for the reductive cross-electrophile coupling of aziridines with aryl halides using nickel electrocatalysis is reported. This reaction provides valuable phenethylamines at room temperature in good yields. The reaction was successfully applied to the electro-reductive cross-coupling of less reactive, unsubstituted N-tosylaziridine. Additionally, we were even able to couple challenging alkyl bromides with aryl aziridines. Control experiments and voltammetric studies confirm that the mechanism is distinct from conventional and photochemical couplings. Furthermore, the role of both Ni(II) organometallic complexes and electrodes was examined, providing insight into the reaction mechanism and the beneficial role of the sacrificial anode in electrochemical cross-couplings.

KW - aziridine

KW - cross-coupling

KW - electrochemical

KW - iron

KW - Lewis acid

KW - nickel

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DO - 10.1021/acscatal.3c01503

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SN - 2155-5435

VL - 13

SP - 8813

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JO - ACS Catalysis

JF - ACS Catalysis

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ER -

Metal Cations from Sacrificial Anodes Act as a Lewis Acid Co-Catalyst in Electrochemical Cross-Coupling of Aryl Bromides and Aziridines

Abstract

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Keywords

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