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Synthesis of 2-Aryl Naphthoquinones by the Cross-Dehydrogenative Coupling Involving an NHC-Catalyzed endo-Stetter Reaction

Arghya Ghosh, Atanu Patra, Subrata Mukherjee, Akkattu T. Biju*

*Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India, Email: atbijuiisc.ac.in

A. Ghosh, A. Patra, S. Mukherjee, A. T. Biju, J. Org. Chem., 2019, 84, 1103-1110.

DOI: 10.1021/acs.joc.8b02931 (free Supporting Information)


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Abstract

An N-heterocyclic carbene (NHC)-catalyzed intramolecular Stetter reaction enables a transition-metal-free and mild cross-dehydrogenative coupling of 2-cinnamoyl benzaldehydes to provide 2-aryl naphthoquinones. The intramolecular Stetter reaction is followed by an aerobic oxidation to reinstall the C-C double bond.

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Key Words

Stetter reaction, cyclization, air, organocatalysis


ID: J42-Y2019