Related Experiment Video
Updated: Jan 8, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Defluorinative Alkene-Carbonyl Coupling Enabled by Photoredox Catalysis: An Access to Allylic Alcohols
Ting-Ting Miao1, Rong-Bin Liang1, Xi Wang1
1College of Chemistry and Chemical Engineering, and Key (Guangdong-Hong Kong Joint) Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Shantou 515063, P. R. China.
Abstract:
The defluorinative coupling of fluoroalkenes with carbonyl compounds provides a direct and efficient strategy to valuable allylic alcohols. However, existing methods typically rely on transition-metal catalyst, stoichiometric reductants, or strongly reducing conditions. Herein, we report a photoredox catalyzed defluorinative coupling between fluoroalkenes and aliphatic carbonyls mediated by ligated boryl radicals, enabling the synthesis of both fluorinated and nonfluorinated allylic alcohols dictated by the choice of fluoroalkene substrate. This transition-metal-free protocol operates under mild conditions, exhibiting high Z/E stereoselectivity and broad substrate scope.
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
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

