Visible‐Light, Photoredox‐Mediated Oxidative Tandem Nitroso‐Diels–Alder Reaction of Arylhydroxylamines with Conjugated Dienes. Issue 15 (30th December 2016)

• Record Type: Journal Article
• Authors: Santacroce, Veronica; Duboc, Raphael; Malacria, Max; Maestri, Giovanni; Masson, Geraldine
• Other Names: König Burkhard guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 15(2017)
• Page Start: 2095
• Page End: 2098
• Publication Date: 2016-12-30
• Subjects: Photocatalysis -- Oxidative tandem -- Nitroso‐Diels–Alder reaction -- Radicals -- Nitrogen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601492
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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 Cl2 afforded 3, 6‐dihydro‐1, 2‐oxazines in good yields under an oxygen atmosphere. Abstract : A visible‐light, photoredox‐mediated oxidative tandem nitroso‐Diels–Alder reaction generates 3, 6‐dihydro‐1, 2‐oxazines from arylhydroxylamines and dienes via intermediary nitrosoarenes in the presence of Ru(bpy)3 Cl2 (bpy = 2, 2′‐bipyridine).