Formation of Sterically Congested C−N Bonds by Electrochemical Reductive Coupling of Amines and α‐Bromocarboxamides

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Abstract: Nucleophilic substitution of α‐bromocarboxamide with amines have been demonstrated to synthesize sterically congested C−N bonds. Electrochemical reductive coupling is an efficient route to access hindered amino acid derivatives possessing a quaternary carbon center with excellent yields under mild reaction conditions. Cyclic voltammetry analyses indicated the cathodic reduction of α‐bromocarboxamides in the presence of amines as nucleophiles. The control experiment using the N‐methyl derivative of α‐bromocarboxamide suggested that the aziridinone is the most probable intermediate in this method.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Formation of Sterically Congested C−N Bonds by Electrochemical Reductive Coupling of Amines and α‐Bromocarboxamides ; day:19 ; month:01 ; year:2024 ; extent:7
ChemElectroChem ; (19.01.2024) (gesamt 7)

Creator: Ghosh, Titli
Kaizawa, Hazuki
Funato, Shohei
Rahman, M. Azadur
Sasaki, Norihiko
Nokami, Toshiki
Abe, Manabu
Nishikata, Takashi

DOI: 10.1002/celc.202300636

URN: urn:nbn:de:101:1-2024011914435243963545

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

Last update: 15.08.2025, 7:22 AM CEST

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Associated

Ghosh, Titli
Kaizawa, Hazuki
Funato, Shohei
Rahman, M. Azadur
Sasaki, Norihiko
Nokami, Toshiki
Abe, Manabu
Nishikata, Takashi

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Formation of Sterically Congested C−N Bonds by Electrochemical Reductive Coupling of Amines and α‐Bromocarboxamides

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Other Objects (12)

New azasilatranes: sterically induced transannular bond weakening and cleavage

Nickel-catalyzed C-N bond activation : activated primary amines as alkylating reagents in reductive cross-coupling

Electrochemical synthesis of peptide aldehydes via C‒N bond cleavage of cyclic amines

Sterically Demanding Oxidative Amidation of α‐Substituted Malononitriles with Amines Using O 2

Sterically Demanding Oxidative Amidation of α‐Substituted Malononitriles with Amines Using O 2

Engineered Biocatalysts for Enantioselective Reductive Aminations of Cyclic Secondary Amines

Rhodium‐Catalysed Reductive Amination for the Synthesis of Tertiary Amines

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General Synthesis of Alkyl Amines via Borrowing Hydrogen and Reductive Amination

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Nickel-catalyzed C-N bond activation : activated primary amines as alkylating reagents in reductive cross-coupling

Electrochemical synthesis of peptide aldehydes via C‒N bond cleavage of cyclic amines

Sterically Demanding Oxidative Amidation of α‐Substituted Malononitriles with Amines Using O 2

Sterically Demanding Oxidative Amidation of α‐Substituted Malononitriles with Amines Using O 2

Engineered Biocatalysts for Enantioselective Reductive Aminations of Cyclic Secondary Amines

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General Synthesis of Alkyl Amines via Borrowing Hydrogen and Reductive Amination

Asymmetric synthesis of γ-branched amines via rhodium-catalyzed reductive amination

General Synthesis of Alkyl Amines via Borrowing Hydrogen and Reductive Amination

Reductive hydroformylation with a selective and highly active rhodium amine system

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Reductive hydroformylation with a selective and highly active rhodium amine system

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