Olefination of Carbonyl Compounds in Ionic Liquids
Dario Lasch1, Tuong Anh To1, Binh Khanh Mai2
1School of Chemistry, University of New South Wales Sydney, Sydney, NSW 2052, Australia.
None:
Carbonyl-olefin and carbonyl-alkyne metathesis (COM and CAM, respectively) reactions convert ubiquitous carbonyl groups directly into C═C bonds. Here we disclose a practical system of Brønsted acid catalysis and an ionic liquid medium that enables both COM and CAM across diverse carbonyl-alkene/alkyne precursors. Pairing a Brønsted acid catalyst with an ionic liquid medium, or simply employing a protic ionic liquid as a dual-role catalyst/solvent system, delivers COM and CAM reactivity in both conventional and mechanochemical settings, connecting catalytic efficiency with scalable, solvent-lean practice.
Related Concept Videos
Reactivity of Enolate Ions
Structures of Aldehydes and Ketones
In aldehydes (Figures 1a and 1b), the carbonyl...
α-Alkylation of Ketones via Enolate Ions
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
Acid Halides to Carboxylic Acids: Hydrolysis
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview


