Synthesis of Benzo-Fused Cycloheptanones from Cyclobutanol Derivatives by a C-C Cleavage/Cross-Coupling/Enolate Arylation Sequence.

Gwyneth L Pudner, Selena Dessain, Eric K Wu, Richmond Sarpong

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Article in Synthesis, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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4 authors.

Gwyneth L PudnerDepartment of Chemistry, University of California-Berkeley, Berkeley, California 94720, USA.

Selena DessainDepartment of Chemistry, University of California-Berkeley, Berkeley, California 94720, USA.

Eric K WuDepartment of Chemistry, University of California-Berkeley, Berkeley, California 94720, USA.

Richmond SarpongDepartment of Chemistry, University of California-Berkeley, Berkeley, California 94720, USA.

Funding

Strategies and Methods for Complex Molecule Synthesis: Acquisition of a 400 MHz Nuclear Magnetic Resonance Spectrometer ConsoleR35GM130345 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI Richmond Sarpong · 2019 to 2026

$5.4M

Acquisition of a Cryoprobe and Related Accessories for a 600 MHz NMR Spectrometer to Support Health Research Activities at the University of California, BerkeleyS10OD024998 · OD · UNIVERSITY OF CALIFORNIA BERKELEY · PI HARTWIG, JOHN F · 2018 to 2018

$265k

NIGMS NIH HHS R35 GM130345NIH HHS S10 OD024998

6 · The paper itself

Abstract

Herein, we describe a convergent method for the synthesis of benzo-fused cycloheptanones from cyclobutanol derivatives and 1,2-dihaloarene electrophiles. The inherent ring strain of the cyclobutanol coupling partner is leveraged to drive a Pd-catalyzed C-C cleavage/cross-coupling. A subsequent intramolecular enolate arylation results in the formation of the benzo-fused seven-membered carbocycle in a one-pot sequence. A range of electronically diverse 1,2-dihaloarene electrophiles as well as various substituted cyclobutanols were investigated as cross-coupling partners.

Indexed as

1,2-dihaloarenesbenzocycloheptanonesC–C cleavagecyclobutanolsone-pot synthesisPd-catalyzed cross-coupling

Identifiers

PMID41404323

DOI10.1055/s-0043-1775469

PMCPMC12705038

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