Issue 28, 2024

Divergent synthesis of multi-substituted phenanthrenes via an internal redox reaction/ring expansion sequence

Abstract

We report an effective synthetic route to multi-substituted phenanthrenes via an internal redox reaction/ring expansion sequence. The interesting feature of the present system is that it allows for the divergent synthesis of the target skeleton depending on the selected Lewis acid catalyst. When benzylidene malonates with a cyclic structure at the ortho-position were treated with BF3·OEt2, three sequential processes (internal redox reaction/elimination of the alkoxy group/ring expansion) proceeded to give phenanthrene derivatives in which the alkoxycarbonyl (CO2R) group and the alkyl (R) group were in close proximity to each other, in good chemical yields. In sharp contrast, treatment with Bi(OTf)3 exclusively led to the formation of another type of phenanthrene, whose R group was positioned distal to the CO2R group.

Graphical abstract: Divergent synthesis of multi-substituted phenanthrenes via an internal redox reaction/ring expansion sequence

Supplementary files

Article information

Article type
Communication
Submitted
19 févr. 2024
Accepted
11 mars 2024
First published
11 mars 2024

Chem. Commun., 2024,60, 3822-3825

Divergent synthesis of multi-substituted phenanthrenes via an internal redox reaction/ring expansion sequence

R. Koyama, M. Anada, S. Sueki, K. Makino, T. Kojima, T. Kawasaki-Takasuka and K. Mori, Chem. Commun., 2024, 60, 3822 DOI: 10.1039/D4CC00797B

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