Catalytic Three-component C–C Bond Forming Dearomatization of Bromoarenes with Malonates and Diazo Compounds

Hiroki Kato; Itsuki Musha; Masaaki Komatsuda; Kei Muto; Junichiro Yamaguchi

doi:10.26434/chemrxiv.12234740.v1

Catalytic Three-component C–C Bond Forming Dearomatization of Bromoarenes with Malonates and Diazo Compounds

Hiroki Kato, Itsuki Musha, Masaaki Komatsuda, Kei Muto, Junichiro Yamaguchi

Research output: Contribution to journal › Article › peer-review

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 of 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.

Original language	English
Journal	Unknown Journal
DOIs	https://doi.org/10.26434/chemrxiv.12234740.v1
Publication status	Published - 2020 May 2

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)
Materials Science(all)

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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 of 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.",

author = "Hiroki Kato and Itsuki Musha and Masaaki Komatsuda and Kei Muto and Junichiro Yamaguchi",

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doi = "10.26434/chemrxiv.12234740.v1",

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T1 - Catalytic Three-component C–C Bond Forming Dearomatization of Bromoarenes with Malonates and Diazo Compounds

AU - Kato, Hiroki

AU - Musha, Itsuki

AU - Komatsuda, Masaaki

AU - Muto, Kei

AU - Yamaguchi, Junichiro

PY - 2020/5/2

Y1 - 2020/5/2

N2 - 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 of 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.

AB - 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 of 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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