Related Experiment Video
Updated: Jan 8, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Flash-Flow Generation and Selective Monoaddition of Organo-Potassium Species to Lactones
Dong-Eun Yoo1, Kazuhiro Okamoto1, Manato Takeda1
1Department of Chemistry, Faculty of Science, Hokkaido University, Kita-ku, Japan.
None:
Fast flash-flow generation of arylpotassium species in a micromixing reactor enables precise synthesis of both functionalized ω-hydroxyarylketones and sequence oligomers, advancing continuous polyester production. The protocol tolerates both electron-rich and electron-deficient aryl bromides as well as diverse six- or seven-membered lactones, cyclic carbonates, and a protected lactam, highlighting broad functional-group compatibility despite high nucleophilicity and basicity of the anionic intermediates. Flash-flow generation of alkoxide termini further enables living anionic ring-opening polymerization: sequential addition of two different lactones provides sequence oligomers with a single monomer unit whose polydispersity was controlled.
More Related Videos
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
Related Concept Videos
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction
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...
Base-Promoted α-Halogenation of Aldehydes and Ketones
Base-Catalyzed Aldol Addition Reaction
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are...
α-Alkylation of Ketones via Enolate Ions