Related Experiment Video
Updated: Jun 8, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Catalytic Aldehyde-Alkyne Couplings Triggered by Ketyl Radicals
Zhi-Xi Xing1, Shu-Sheng Chen1, Huan-Ming Huang1
1School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China.
Abstract:
A general and flexible platform for catalytic aldehyde-alkyne couplings triggered by ketyl radicals is described. This open-shell strategy necessitates only a catalytic quantity of a photoredox catalyst, along with Hünig's base (DIPEA) as a halogen atom transfer reagent. The reaction proceeds through sequential steps involving activation, halogen atom transfer, and radical addition. This carbonyl-alkyne coupling exhibits a wide substrate scope and functional group compatibility and has been successfully applied to the late-stage modification of complex architectures.
Related Concept Videos
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Alkynes to Carboxylic Acids: Oxidative Cleavage
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
The carbonyl center is...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Radical Reactivity: Electrophilic Radicals

