Issue 33, 2020

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
21 maj 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
Creative Commons BY license

Chem. Sci., 2020,11, 8779-8784

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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