Issue 18, 2020

Photocatalytic xanthate-based radical addition/cyclization reaction sequence toward 2-biphenyl isocyanides: synthesis of 6-alkylated phenanthridines

Abstract

A photocatalytic xanthate-based radical addition/cyclization reaction cascade toward 2-biphenylisocyanides is described as a practical and modular approach to 6-alkylated phenanthridines. The use of xanthates as radical precursors allowed the synthesis of diversely 6-substituted phenanthridines. Electrophilic radicals derived from nitriles, aromatic and aliphatic ketones, malonates, and amide derivatives, as well as radicals derived from phthalimidomethyl and benzylic derivatives were successfully introduced. The reaction proceeds under mild conditions without a stoichiometric amount of oxidant. Thirty novel phenanthridine scaffolds were synthesized with yields ranging from 24 to 76%.

Graphical abstract: Photocatalytic xanthate-based radical addition/cyclization reaction sequence toward 2-biphenyl isocyanides: synthesis of 6-alkylated phenanthridines

Supplementary files

Article information

Article type
Communication
Submitted
21 jan 2020
Accepted
21 apr 2020
First published
22 apr 2020

Org. Biomol. Chem., 2020,18, 3487-3491

Photocatalytic xanthate-based radical addition/cyclization reaction sequence toward 2-biphenyl isocyanides: synthesis of 6-alkylated phenanthridines

P. López-Mendoza and L. D. Miranda, Org. Biomol. Chem., 2020, 18, 3487 DOI: 10.1039/D0OB00136H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements