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

preprint
submitted on 02.05.2020 and posted on 05.05.2020 by Hiroki Kato, Itsuki Musha, Masaaki Komatsuda, Kei Muto, Junichiro Yamaguchi
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.

Funding

JP19H02726

JP20H04829

JP19K15573

The SATOMI Scholarship Foundation

History

Email Address of Submitting Author

junyamaguchi@waseda.jp

Institution

Waseda University

Country

Japan

ORCID For Submitting Author

0000-0002-3896-5882

Declaration of Conflict of Interest

No competing financial interests have been declared.

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