Aerobic Tetrazine‐Catalyzed Oxidative Nitroso‐Diels‐Alder Reaction of N‐Arylhydroxylamines with Dienecarbamates: Access to Functionalized 1,6‐Dihydro‐1,2‐oxazines - Université Paris-Saclay Accéder directement au contenu
Article Dans Une Revue ChemCatChem Année : 2019

Aerobic Tetrazine‐Catalyzed Oxidative Nitroso‐Diels‐Alder Reaction of N‐Arylhydroxylamines with Dienecarbamates: Access to Functionalized 1,6‐Dihydro‐1,2‐oxazines

Résumé

A new organocatalytic and environmentally friendly aerobic oxidative-catalyzed nitroso-Diels-Alder (NDA) reaction of Narylhydroxylamines with dienecarbamates has been developed. 3,6-Bis(2,2,2-trifluoroethoxy)-s-tetrazine) was found to be an effective catalyst to selectively oxidize various N-arylhydroxylamines in the presence of molecular oxygen, but in the absence of photostimulation, as a terminal oxidant. In addition, active catalytic species can be generated in situ from commercially available 3,6-dichlorotetrazine.
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hal-02324655 , version 1 (25-11-2020)

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Tuan Le, Thibaut Courant, Jérémy Merad, Clémence Allain, Pierre Audebert, et al.. Aerobic Tetrazine‐Catalyzed Oxidative Nitroso‐Diels‐Alder Reaction of N‐Arylhydroxylamines with Dienecarbamates: Access to Functionalized 1,6‐Dihydro‐1,2‐oxazines. ChemCatChem, 2019, ⟨10.1002/cctc.201901373⟩. ⟨hal-02324655⟩
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