Related Experiment Video
Updated: May 31, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
On the nature of the oxidative heterocoupling of lithium enolates
Brian M Casey1, Robert A Flowers
1Department of Chemistry, Lehigh University, Bethlehem, Pennsylvania 18015, USA.
Abstract:
The coupling of enolates through single-electron oxidation is one of the most direct routes for generating 1,4-dicarbonyls. Recent work on the intermolecular heterocoupling of equimolar amounts of two different enolates through single-electron oxidation has shown that synthetically useful yields beyond those predicted by statistics can be obtained. To determine the underlying basis for the selective formation of heterocoupled products, kinetic, (7)Li NMR, and synthetic studies were performed. The collection of data obtained from these experiments shows that the selective formation of heterocoupled products is a consequence of heteroaggregation of lithium enolates.
Related Concept Videos
Reactivity of Enolate Ions
α-Alkylation of Ketones via Enolate Ions
Regioselective Formation of Enolates
Stereochemical Effects of Enolization
Enolate Mechanism Conventions
C-attack...
Reactivity of Enols

