Article Dans Une Revue Organic Chemistry Frontiers Année : 2025

Synthesis of non-symmetric ortho-functionalized azoarenes through arylation of arylazo sulfones

Résumé

A novel protocol for the arylation of arylazo sulfones with organomagnesiums for accessing non-symmetric ortho-functionalized azoarenes has been succesfully developped. Bench-stable substituted arylazo sulfones, which serve as masked electrophilic diazo sources, have been effectively arylated, achieving good to excellent isolated yields. This method demonstrates broad tolerance towards a wide variety of substituents. Further, the mechanism and the regioselectivity of the addition has been investigated using DFT calculations. The observed regioselectivity would arise from a combination of steric and electronic effects, as well as the presence or absence of a strongly coordinating substituent at the ortho position of the starting material.

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hal-05407069 , version 1 (09-12-2025)

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Rayhane Hammami, Victor Flon, Morgane Sanselme, Julien Legros, Isabelle Chataigner, et al.. Synthesis of non-symmetric ortho-functionalized azoarenes through arylation of arylazo sulfones. Organic Chemistry Frontiers, 2025, 12 (24), pp.6953-6960. ⟨10.1039/D5QO00932D⟩. ⟨hal-05407069⟩
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