Related Experiment Video
Updated: Apr 20, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Bimetallic zinc complex--active species in coupling of terminal alkynes with aldehydes via nucleophilic
Jiwen Yuan1, Jing Wang, Guanghui Zhang
1College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, P. R. China. aiwenlei@whu.edu.cn chao.liu@whu.edu.cn.
Abstract:
A mechanistic study on the zinc-promoted coupling between aldehydes and terminal alkynes via nucleophilic addition/Oppenauer oxidation using operando IR, XANES/EXAFS techniques and DFT calculations was demonstrated. It was determined that a bimetallic zinc complex was the active species.
Related Concept Videos
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
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.
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Radical Anti-Markovnikov Addition to Alkenes: Mechanism
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
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.
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

