Related Experiment Video
Updated: Jan 1, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Decarbonylative Olefination of Aldehydes to Alkenes
Diana Ainembabazi1, Christopher Reid1, Amanda Chen1
1Chemistry Department , George Washington University , 800 22nd Street NW , Washington , D.C. 20052 , United States.
Abstract:
New atom-economical alternatives to Wittig chemistry are needed to construct olefins from carbonyl compounds, but none have been developed to-date. Here we report an atom-economical olefination of carbonyls via aldol-decarbonylative coupling of aldehydes using robust and recyclable supported Pd catalysts, producing only CO and H2O as waste. The reaction affords homocoupling of aliphatic aldehydes, as well as heterocoupling of aliphatic and aromatic ones. Computations provide insight into the selectivity and thermodynamics of the reaction. The tandem aldol-decarbonylation reaction opens the door to exploration of new carbonyl reactivity to construct olefins.
Related Concept Videos
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives
Carboxylic acid derivatives like acid chlorides and esters are more easily reducible than the corresponding acids. The derivatives reduce in the presence of mild reducing agents to give aldehydes. Aldehydes can also be prepared by Rosenmund reduction, that is, the reduction of...
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
The carbonyl center is activated by...

