Synthesis of Cyclopropylamines through an Electro-Induced Hofmann Rearrangement

Thomas Cantin; André B. Charette; Thomas Poisson; Philippe Jubault

doi:10.1055/a-2050-9368

Synthesis, Table of Contents

Synthesis 2023; 55(18): 2943-2950
DOI: 10.1055/a-2050-9368

paper

Special Issue Electrochemical Organic Synthesis

Synthesis of Cyclopropylamines through an Electro-Induced Hofmann Rearrangement

Thomas Cantin

^aNormandie Univ., INSA Rouen Normandie, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France

,

André B. Charette ∗

^bUniversité de Montréal, FRQ-NT Centre in Green Chemistry and Catalysis Department of Chemistry, 1375, av. Thérèse Lavoie-Roux, Montréal, QC H2 V 0B3, Canada

,

Thomas Poisson ∗

^aNormandie Univ., INSA Rouen Normandie, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France

,

Philippe Jubault∗

^aNormandie Univ., INSA Rouen Normandie, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France

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Abstract

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Abstract

A practical access to cyclopropylamines from the corresponding amides is disclosed, according to an electro-induced Hofmann rearrangement. In an undivided cell under galvanostatic conditions, a panel of cyclopropyl amides was readily converted into the corresponding amines (17 examples, 23% to 94% yield). This reaction allowed an easy access to the versatile cyclopropylamines and is complementary to the existing methods.

Key words

cyclopropanes - electrochemistry - Hofmann rearrangement - synthetic method

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References

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