Work

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

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c02218

Authors: Katarzyna Doktor, Julien C. Vantourout, Quentin Michaudel

Institutions: Texas A&M University, Syngenta (Switzerland)

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: FACE Foundation, National Institutes of Health, National Institute of General Medical Sciences