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Expeditious synthesis of phenanthridines through a Pd/MnO2-mediated C–H arylation/oxidative annulation cascade from aldehydes, aryl iodides and amino acids

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Abstract

The expeditious construction of phenanthridine scaffolds via a Pd/MnO2-mediated C–H arylation/oxidative annulation cascade involving aldehydes, aryl iodides and amino acids is disclosed. This reaction proceeds smoothly involving the formation of multiple chemical bonds with the tolerance of a wide range of functional groups. The control experiments suggest a radical mechanism for C–N bond formation via MnO2-promoted oxidative annulation of imine compounds. The synthetic utility of this transformation has been demonstrated via the straightforward access to bioactive natural alkaloid trisphaeridine and its analogue.

Graphical abstract: Expeditious synthesis of phenanthridines through a Pd/MnO2-mediated C–H arylation/oxidative annulation cascade from aldehydes, aryl iodides and amino acids

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Article information


Submitted
12 Jan 2020
Accepted
29 Jan 2020
First published
29 Jan 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Expeditious synthesis of phenanthridines through a Pd/MnO2-mediated C–H arylation/oxidative annulation cascade from aldehydes, aryl iodides and amino acids

J. Fan, L. Li, J. Zhang and M. Xie, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC00300J

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