Visible Light Mediated Photocatalytic N‑Radical Cascade Reactivity of γ,δ-Unsaturated N‑Arylsulfonylhydrazones: A General Approach to Structurally Diverse Tetrahydropyridazines

Tetrahydropyridazines are of particular interest for their versatility as intermediates in organic synthesis and display pharmacological activity in several domains. Here, we describe the photocatalytic synthesis of different tetrahydropyridazines starting from γ,δ-unsaturated N-arylsulfonylhydrazon...

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Published in:Journal of organic chemistry 2021-02, Vol.86 (4), p.3300-3323
Main Authors: Azzi, Emanuele, Ghigo, Giovanni, Parisotto, Stefano, Pellegrino, Francesco, Priola, Emanuele, Renzi, Polyssena, Deagostino, Annamaria
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cited_by cdi_FETCH-LOGICAL-a341t-2386fd33991c078d0cf4b8322db92429bb2d9551cd86dcf4458c15392433f8f93
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container_end_page 3323
container_issue 4
container_start_page 3300
container_title Journal of organic chemistry
container_volume 86
creator Azzi, Emanuele
Ghigo, Giovanni
Parisotto, Stefano
Pellegrino, Francesco
Priola, Emanuele
Renzi, Polyssena
Deagostino, Annamaria
description Tetrahydropyridazines are of particular interest for their versatility as intermediates in organic synthesis and display pharmacological activity in several domains. Here, we describe the photocatalytic synthesis of different tetrahydropyridazines starting from γ,δ-unsaturated N-arylsulfonylhydrazones. Simple structural changes of substrates result into three different pathways beginning from a common N-hydrazonyl radical, which evolves through a domino carboamination/dearomatization, a HAT process, or a photoinduced radical Smiles rearrangement to afford diverse tetrahydropyridazines. All reactions are carried out in very mild conditions, and the quite inexpensive [Ru­(bpy)3]­Cl2 is used as the catalyst. Preliminary mechanism studies are presented, among them luminescence and electrochemical characterization of the involved species. Computational studies allow to rationalize the mechanism in accord with the experimental findings.
doi_str_mv 10.1021/acs.joc.0c02605
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title Visible Light Mediated Photocatalytic N‑Radical Cascade Reactivity of γ,δ-Unsaturated N‑Arylsulfonylhydrazones: A General Approach to Structurally Diverse Tetrahydropyridazines
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