Discovery and Development of an Aerobic Radical Hydroxyarylation Reaction Using Aryl Halides, Olefins, and O2
Mark C. Maust, Defne Tuncaral, Simon B. Blakey
TL;DR
Scientists developed a new chemical reaction that uses light and oxygen to create complex ring structures from simple starting materials.
Contribution
A novel aerobic radical hydroxyarylation reaction is introduced, enabling mild synthesis of hydroxylated ring systems.
Findings
Photoredox activation generates aryl radicals for hydroxyarylation under mild conditions.
The reaction enables 5-exo, 6-exo, and dearomative cyclizations to form fused ring systems.
Iodide is identified as essential in the catalytic cycle when using aryl bromides.
Abstract
Herein, we report the development of a radical hydroxyarylation reaction through the coupling of an aryl radical, an olefin, and O2. Photoredox activation of a silyl radical halogen atom abstractor enables mild aryl radical generation and reactivity in 5-exo, 6-exo, and dearomative cyclizations to synthesize a variety of hydroxylated semisaturated fused ring systems. Expansion of the substrate scope to include aryl bromide starting materials reveals the crucial role of iodide in the catalytic cycle.
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Taxonomy
TopicsRadical Photochemical Reactions · Oxidative Organic Chemistry Reactions · Catalytic C–H Functionalization Methods