Electrocatalytic Reduction of (Hetero) Aryl Halides in a Proton‐Exchange Membrane Reactor and its Application for Deuteration

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Abstract: We developed an electrocatalytic reduction of (hetero) aryl halides under mild conditions using a proton exchange membrane (PEM) reactor. This approach allows substituting the halogeno groups on the aryl rings to protons by water and electron. Taking advantage of this transformation, deuterodehalogenation of (hetero) aryl halides, which forms mono‐deuterated (hetero) aryls, was demonstrated using heavy water as a deuterium source. The current efficiency and deuterium ratio could be increased by the conditions optimized by machine‐learning method, Bayesian optimization.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Electrocatalytic Reduction of (Hetero) Aryl Halides in a Proton‐Exchange Membrane Reactor and its Application for Deuteration ; day:12 ; month:09 ; year:2023 ; extent:7
ChemElectroChem ; (12.09.2023) (gesamt 7)

Creator: Ashikari, Yosuke
Mandai, Kyoko
Yao, Yiyue
Tsuchihashi, Yuta
Nagaki, Aiichiro

DOI: 10.1002/celc.202300315

URN: urn:nbn:de:101:1-2023091315241232427820

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 10:55 AM CEST

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Ashikari, Yosuke
Mandai, Kyoko
Yao, Yiyue
Tsuchihashi, Yuta
Nagaki, Aiichiro

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Hochschulschrift

Palladium-catalyzed carbonylation reactions of aryl halides

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Palladium-catalyzed carbonylation reactions of aryl halides

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Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

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A Practical Method for Continuous Production of sp3‐Rich Compounds from (Hetero) Aryl Halides and Redox‐Active Esters

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Hochschulschrift

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Electrocatalytic Reduction of (Hetero) Aryl Halides in a Proton‐Exchange Membrane Reactor and its Application for Deuteration

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Other Objects (12)

Scalable, Chemoselective Nickel Electrocatalytic Sulfinylation of Aryl Halides with SO 2

Scalable, Chemoselective Nickel Electrocatalytic Sulfinylation of Aryl Halides with SO 2

Cobalt‐Catalyzed Cross‐Coupling of Functionalized Alkylzinc Reagents with (Hetero) Aryl Halides

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C−S/C−N Couplings

A Practical Method for Continuous Production of sp3‐Rich Compounds from (Hetero) Aryl Halides and Redox‐Active Esters

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Atomic Dispersed Hetero-Pairs for Enhanced Electrocatalytic CO2 Reduction

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides

Synthesis of Non‐Symmetric Azoarenes by Palladium‐Catalyzed Cross‐Coupling of Silicon‐Masked Diazenyl Anions and (Hetero)Aryl Halides

Synthesis of Non‐Symmetric Azoarenes by Palladium‐Catalyzed Cross‐Coupling of Silicon‐Masked Diazenyl Anions and (Hetero) Aryl Halides

Palladium-catalyzed carbonylation reactions of aryl halides

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Cobalt‐Catalyzed Cross‐Coupling of Functionalized Alkylzinc Reagents with (Hetero) Aryl Halides

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C−S/C−N Couplings

A Practical Method for Continuous Production of sp3‐Rich Compounds from (Hetero) Aryl Halides and Redox‐Active Esters

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Atomic Dispersed Hetero-Pairs for Enhanced Electrocatalytic CO2 Reduction

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides

Synthesis of Non‐Symmetric Azoarenes by Palladium‐Catalyzed Cross‐Coupling of Silicon‐Masked Diazenyl Anions and (Hetero)Aryl Halides

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Palladium-catalyzed carbonylation reactions of aryl halides

Scalable, Chemoselective Nickel Electrocatalytic Sulfinylation of Aryl Halides with SO 2

Scalable, Chemoselective Nickel Electrocatalytic Sulfinylation of Aryl Halides with SO 2

Cobalt‐Catalyzed Cross‐Coupling of Functionalized Alkylzinc Reagents with (Hetero) Aryl Halides

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C−S/C−N Couplings

A Practical Method for Continuous Production of sp3‐Rich Compounds from (Hetero) Aryl Halides and Redox‐Active Esters

μProspects and Applications of Palladium Nanoparticles in the Cross‐coupling of (hetero)aryl Halides and Related Analogues

Atomic Dispersed Hetero-Pairs for Enhanced Electrocatalytic CO2 Reduction

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides

Synthesis of Non‐Symmetric Azoarenes by Palladium‐Catalyzed Cross‐Coupling of Silicon‐Masked Diazenyl Anions and (Hetero)Aryl Halides

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