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Updated: Jan 8, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Synthesis of Benzo-Fused Cycloheptanones from Cyclobutanol Derivatives by a C-C Cleavage/Cross-Coupling/Enolate
Gwyneth L Pudner1, Selena Dessain1, Eric K Wu1
1Department of Chemistry, University of California-Berkeley, Berkeley, California 94720, USA.
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.
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