How to Confidently Become an Electrosynthetic Practitioner

Charvet, Sylvain; Kerackian, Taline; Rubel, Camille Z.; Vantourout, Julien C.

doi:10.1002/9781119855668.ch3

Enabling Tools and Techniques for Organic Synthesis 2023

DOI: 10.1002/9781119855668.ch3

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How to Confidently Become an Electrosynthetic Practitioner

Sylvain Charvet,

Taline Kerackian,

Camille Z. Rubel

et al.

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2024

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Cited by 2 publications

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A Unified Synthesis of Diazenes from Primary Amines Using a SuFEx/Electrochemistry Strategy

Doktor,

Vantourout,

Michaudel

2024

Org. Lett.

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The electrochemical synthesis of 1,2-disubsituted diazenes via anodic oxidation of bench stable symmetrical and unsymmetrical sulfamides is reported. This work capitalizes on the streamlined preparation of diverse N,N′-disubstituted sulfamides using Sulfur(VI) Fluoride Exchange (SuFEx) click chemistry that were subsequently subjected to electrochemical oxidation to afford the desired diazenes. The electrochemical nature of the reaction conditions obviated the need for chlorinating reagents, which considerably improved the sustainability of the overall process. Noteworthy, in addition to the synthesis of alkyl diazenes, these milder conditions were shown to be competent for the formation of azobenzenes, albeit in lower yields. Mechanistic experiments were conducted to delineate the reaction pathway and to rationalize the formation of side products observed during the electro-oxidation of N,N'-diarylsulfamides.

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A Unified Synthesis of Diazenes from Primary Amines Using a SuFEx/Electrochemistry Strategy

Doktor,

Vantourout,

Michaudel

2024

Org. Lett.

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Electrochemical Postpolymerization Modification and Deconstruction of Macromolecules

Marquez,

Gitter,

Gilchrist

et al. 2024

ACS Macro Lett.

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Electrolysis is an emerging approach to polymer postpolymerization modification, deconstruction, and depolymerization. Electrochemical reactions are particularly appealing for macromolecular transformations because of their high selectivity, ability to be externally monitored, and intrinsic scalability. Despite these desirable features and the recent resurgent use of smallmolecule electrochemical reactions, the development of macromolecular electrolysis has been limited. Herein, we highlight recent examples of polymer transformations driven by heterogeneous redox chemistry. Throughout our exploration of macromolecular electrolysis, we provide our perspective on opportunities for continued investigation in this nascent field. Specifically, we highlight how targeted reaction development through deeper mechanistic insight will expand the scope of materials that can be (de)constructed with electrochemical methods. As this insight is developed, we expect macromolecular electrolysis to emerge as a high-functioning and complementary tool for macromolecular functionalization and deconstruction.

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How to Confidently Become an Electrosynthetic Practitioner

Cited by 2 publications

References 38 publications

A Unified Synthesis of Diazenes from Primary Amines Using a SuFEx/Electrochemistry Strategy

A Unified Synthesis of Diazenes from Primary Amines Using a SuFEx/Electrochemistry Strategy

Electrochemical Postpolymerization Modification and Deconstruction of Macromolecules

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