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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.

SUBMITTER: Kato H

PROVIDER: S-EPMC8163412 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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

Kato Hiroki H Musha Itsuki I Komatsuda Masaaki M Muto Kei K Yamaguchi Junichiro J

Chemical science 20200729 33

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 throu ...[more]

PMID: 34123130

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