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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Bioinspired Photoredox Benzylation of Quinones
Maxime Donzel1, Mourad Elhabiri1, Elisabeth Davioud-Charvet1
1Laboratoire d'Innovation Moléculaire et Applications (LIMA) Team Bio(IN)organic and Medicinal Chemistry, European School of Chemistry, Polymers and Materials (ECPM), Université de Strasbourg-CNRS-UHA UMR7042, 25 Rue Becquerel, Strasbourg 67087, France.
Abstract:
3-Benzylmenadiones were obtained in good yield by using a blue-light-induced photoredox process in the presence of Fe(III), oxygen, and γ-terpinene acting as a hydrogen-atom transfer agent. This methodology is compatible with a wide variety of diversely substituted 1,4-naphthoquinones as well as various cheap, readily available benzyl bromides with excellent functional group tolerance. The benzylation mechanism was investigated and supports a three-step radical cascade with the key involvement of the photogenerated superoxide anion radical.
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