4.8 Article

Aerobic Oxidative N-Heterocyclic Carbene-Catalyzed Formal [3+3] Cyclization for the Synthesis of Tetrasubstituted Benzene Derivatives

Journal

ORGANIC LETTERS
Volume 24, Issue 49, Pages 9146-9150

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03879

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This study presents an accessible aerobic N-heterocyclic carbene (NHC)-catalyzed method for efficiently producing tetrasubstituted benzene rings in a single reaction. The method uses atmospheric oxygen (O2) as the terminal oxidant and employs electron transfer mediators to orchestrate an aerobic oxidation reaction.
Herein, we present an accessible aerobic N-heterocyclic carbene (NHC)-catalyzed method that efficiently produces tetrasubstituted benzene rings in a single reaction. The method employs atmospheric oxygen (O2) as the terminal oxidant in a reaction that requires two oxidative steps. The aerobic oxidation is achieved by a selection of electron transfer mediators orchestrating a redox cascade, turning a high-energy aerobic oxidation reaction pathway into a favorable process.

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