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Updated: Aug 13, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
One-pot sequential Cu-catalyzed reduction and Pd-catalyzed arylation of silyl enol ethers
Junghyun Chae1, Jaesook Yun, Stephen L Buchwald
1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Abstract:
[reaction: see text] Enantiomerically enriched beta-substituted diphenylsilyl enol ethers, which can be prepared from Cu-catalyzed asymmetric conjugate reduction, are utilized in the Pd-catalyzed arylation of various aryl bromides. This new method provides a simple route to alpha-arylated cycloalkanones with excellent levels of enantiomeric and diastereomeric purity. The isolation of the intermediate, diphenylsilyl enol ethers is not necessary; the procedure can be carried out in one-pot.
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