Related Experiment Video
Updated: May 12, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
A General Direct Aldehyde C-H Alkylation via TBADT-Nickel Synergistic Catalysis
Zhimin Hu1, Ji-Wei Sang1, Shize Xie1
1Department of Phytochemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China.
Abstract:
Herein, we present a nickel/tetrabutylammonium decatungstate (TBADT)-catalyzed protocol for general C-H alkylation of aldehydes, enabling the efficient synthesis of aliphatic ketones through ligand-controlled cross-coupling. This mild and cost-effective methodology demonstrates broad substrate compatibility with various commercially available aldehydes and both activated and unactivated alkyl bromides, delivering target products in high yields. Notably, the practical utility of this catalytic system has been highlighted through a concise two-step synthesis of the commercially valuable musk odorant Aurelione from readily available starting materials.
More Related Videos
12:08Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
Published on: June 24, 2022
07:06A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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.
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.
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction