Metal-Free Electrocyclization at Ambient Temperature: Synthesis of 1-Arylcarbazoles

Rajarshi Samanta; Katharina Kulikov; Carsten Strohmann; Andrey P. Antonchick

doi:10.1055/s-0032-1316743

Synthesis, Table of Contents

Synthesis 2012; 44(15): 2325-2332
DOI: 10.1055/s-0032-1316743

feature article

Metal-Free Electrocyclization at Ambient Temperature: Synthesis of 1-Arylcarbazoles

Rajarshi Samanta

^aMax Planck Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany

,

Katharina Kulikov

^aMax Planck Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany

^bTU Dortmund, Faculty of Chemistry, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany, Email: andrey.antonchick@mpi-dortmund.mpg.de

,

Carsten Strohmann

^bTU Dortmund, Faculty of Chemistry, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany, Email: andrey.antonchick@mpi-dortmund.mpg.de

,

Andrey P. Antonchick*

^aMax Planck Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany

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Abstract

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Abstract

An efficient novel protocol for the construction of an hyellazole-inspired compound collection is described. Starting from 2,6-diarylacetanilides, the desired products were obtained using hypervalent iodine promoted electrocyclization. The mechanism of product formation was investigated through intramolecular competition experiments.

Key words

alkaloids - heterocycles - electrocyclization - hypervalent iodine - biaryls

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References

References

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