Work

On the Nature of the Oxidative Heterocoupling of Lithium Enolates

Year: 2011

Type: article

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.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja205017e

Authors: Brian M. Casey, Robert A. Flowers

Institution: Lehigh University

Language: English

Topic: Coordination Chemistry and Organometallics

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: Mechanism Based Design of Ce(IV) Mediated Reactions