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Issue 31, 2020
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Iron-mediated deuterium addition cascade cyano insertion/cyclization of N-arylacrylamides to access deuterium-labelled phenanthridines

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Abstract

Deuterated molecules feature important biological activities and pharmacokinetic properties for the design of pharmaceuticals. Radical cyclization cascades involving the deuteration of alkenes to form heterocyclic compounds have rarely been reported. Herein, a deuterium addition cascade cyano insertion/cyclization of N-arylacrylamides to synthesize deuterated phenanthridines is described. Cheap Fe(NO3)3·9H2O enables the generation of a deuterium radical from NaBD4in situ. These reactions proceed under mild conditions in a short time and a variety of functional groups are well tolerated.

Graphical abstract: Iron-mediated deuterium addition cascade cyano insertion/cyclization of N-arylacrylamides to access deuterium-labelled phenanthridines

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Article information


Submitted
08 Jun 2020
Accepted
19 Jul 2020
First published
20 Jul 2020

Org. Biomol. Chem., 2020,18, 6126-6133
Article type
Paper

Iron-mediated deuterium addition cascade cyano insertion/cyclization of N-arylacrylamides to access deuterium-labelled phenanthridines

L. Ji, W. Gu, P. Liu and P. Sun, Org. Biomol. Chem., 2020, 18, 6126
DOI: 10.1039/D0OB01178A

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