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Issue 33, 2020
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Catalytic three-component C–C bond forming dearomatization of bromoarenes with malonates and diazo compounds

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Abstract

A Pd-catalyzed dearomative three-component C–C bond formation of bromoarenes with diazo compounds and malonates was developed. Various bromoarenes ranging from benzenoids to azines and heteroles were transformed to the corresponding substituted alicyclic molecules. The key to this reaction is the generation of a benzyl–palladium intermediate, which reacts with malonates to form a Pd–O-enolate species. Strikingly, the present method enabled rapid access to multi-substituted alicycles through subsequent elaboration of dearomatized products.

Graphical abstract: Catalytic three-component C–C bond forming dearomatization of bromoarenes with malonates and diazo compounds

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Supplementary files

Article information


Submitted
21 May 2020
Accepted
29 Jul 2020
First published
29 Jul 2020

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

Chem. Sci., 2020,11, 8779-8784
Article type
Edge Article

Catalytic three-component C–C bond forming dearomatization of bromoarenes with malonates and diazo compounds

H. Kato, I. Musha, M. Komatsuda, K. Muto and J. Yamaguchi, Chem. Sci., 2020, 11, 8779
DOI: 10.1039/D0SC02881A

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