4.5 Article

Visible-Light, Photoredox-Mediated Oxidative Tandem Nitroso-Diels-Alder Reaction of Arylhydroxylamines with Conjugated Dienes

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 15, Pages 2095-2098

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201601492

Keywords

Photocatalysis; Oxidative tandem; Nitroso-Diels-Alder reaction; Radicals; Nitrogen heterocycles

Funding

  1. Centre National de la Recherche Scientifique (CNRS)
  2. Universita degli Studi di Parma
  3. Ministero dell'Universita e della Ricerca (MIUR)
  4. Scientific Independence of Young Researchers (SIR) program [RBSI14NKFL]

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Arylhydroxylamines were used in the nitroso-Diels-Alder reaction to generate in situ nitrosoarenes under visible-light, catalytic and aerobic conditions. Mixing a solution of aryl- or heteroarylhydroxylamines with conjuguated dienes in the presence of a catalytic amount of Ru(bpy)(3)Cl-2 afforded 3,6-dihydro-1,2-oxazines in good yields under an oxygen atmosphere.

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