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Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation

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Abstract

Cubane (C8H8), a cubic alkane, has long attracted attention owing to its unique 3D structure. In order to utilize the cubane scaffold widely in science and technology, a powerful method for synthesizing diverse cubane derivatives is required. Herein, we report the synthesis of mono-, di-, tri-, and tetra-arylated cubanes. Directed ortho-metalation with lithium base/alkyl zinc and subsequent palladium-catalyzed arylation enabled C–H metalation and arylation of cubane. This reaction allows the late-stage and regioselective installation of a wide range of aryl groups, realizing the first programmable synthesis of diverse multiply arylated cubanes.

Graphical abstract: Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation

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Article information


Submitted
03 Apr 2020
Accepted
23 Apr 2020
First published
24 Apr 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation

R. Okude, G. Mori, A. Yagi and K. Itami, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC01909G

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