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Updated: Mar 3, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
An Increased Understanding of Enolate Additions under Mechanochemical Conditions
1Department of Chemistry, University of Cincinnati, Cincinnati, OH 45221-0172, USA. hopgoohm@mail.uc.edu.
Abstract:
Very little is known about enolate addition chemistry under solver-free mechanochemical conditions. In this report, we investigated the ability to selectively form products arising from the primary, secondary, and tertiary enolates under solvent-free conditions. Using potassium tert-butoxide as the base and primary, secondary, and tertiary electrophiles, we were able to generate various enolate addition products including, 1,3,3,3-tetraphenyl-2,2-dimethyl-1-propanone; a molecule we did not observe under traditional solution-based conditions.
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