Related Experiment Video
Updated: May 19, 2026

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
Published on: August 17, 2018
Transient Directing Group-Enabled Palladium-Catalyzed Axially Chiral C-H Alkynylation
Yao-Yao Liu1,2,3,4, Yin-Xu Zhao1,2, Jia-Qi Chen3,4
1State Key Laboratory of Coordination Chemistry, School of Chemistry, Nanjing University, Nanjing 210023, China.
None:
Efficient and modular approaches to accessing diverse atropisomers remain challenging. We reported a palladium-catalyzed enantioselective C-H alkynylation of styrene derivatives via a transient directing group (TDG) strategy, affording axially chiral styrenes under mild conditions with high enantioselectivity. Pyrrole-based transient chiral auxiliaries obtained by computationally assisted design played critical roles in both transient directing group formation and stereochemical control. Computational studies revealed that enhanced auxiliary rigidity and multiple noncovalent interactions enabled effective enantiodifferentiation. The resulting axially chiral aldehydes are versatile platforms, readily converting into valuable chiral molecules such as carboxylic acids and alcohols in one step. Notably, the derived chiral carboxylic acids act as competent ligands for asymmetric catalysis, highlighting the synthetic utility and broader potential of this strategy.
More Related Videos
06:46Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
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...
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
α-Alkylation of Ketones via Enolate Ions
Diazonium Group Substitution: –OH and –H