Horner–Wadsworth–Emmons reaction
| Horner–Wadsworth–Emmons reaction | |
|---|---|
| Named after | Leopold Horner William S. Wadsworth William D. Emmons |
| Reaction type | Coupling reaction |
| Identifiers | |
| Organic Chemistry Portal | wittig-horner-reaction |
| RSC ontology ID | RXNO:0000056 |
The Horner–Wadsworth–Emmons (HWE) reaction is a chemical reaction used in organic chemistry of stabilized phosphonate carbanions with aldehydes (or ketones) to produce predominantly E-alkenes.
In 1958, Leopold Horner published a modified Wittig reaction using phosphonate-stabilized carbanions. William S. Wadsworth and William D. Emmons further defined the reaction.
In contrast to phosphonium ylides used in the Wittig reaction, phosphonate-stabilized carbanions are more nucleophilic but less basic. Likewise, phosphonate-stabilized carbanions can be alkylated. Unlike phosphonium ylides, the dialkylphosphate salt byproduct is easily removed by aqueous extraction.
Several reviews have been published.