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Updated: Nov 2, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Catalytic three-component C-C bond forming dearomatization of bromoarenes with malonates and diazo compounds
Hiroki Kato1, Itsuki Musha1, Masaaki Komatsuda1
1Department of Applied Chemistry, Waseda University 3-4-1, Ohkubo, Shinjuku Tokyo 169-8555 Japan junyamaguchi@waseda.jp.
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.
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