Related Experiment Video
Updated: Aug 17, 2025

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
Published on: February 27, 2017
Palladium-Catalyzed Difunctionalization of Norbornenes via Arylation and Alkynylation
Yijun Shi1, Chong-Lei Ji2, Chengwei Liu3,4
1Shandong Lunan Coal Chemical Research Institute of Engineering and Technology, Zaozhuang University, 1 Bei'an Road, Zaozhuang, Shandong277160, China.
Abstract:
We report the first general and practical method for the addition of aryl halides and alkynes to norbornenes with palladium catalysis. Norbornenes have been used as the unsaturated acceptors of aryl and alkynyl groups to construct saturated bridged C-C bonds. The combination of Pd(OAc)2/PCy3HBF4 has been identified as the optimal system promoting difunctionalization of norbornenes via the C-X/C-H bond cleavage and highly selective C(sp3)-C(sp2)/C(sp3)-C(sp) bond formation. Broad substrate scope and excellent functional group tolerance have been achieved to show the high efficiency of this approach. Mechanism studies based on experiments and DFT have been performed to gain insights into the catalytic mechanism.
More Related Videos
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
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
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
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.
Nucleophilic Aromatic Substitution: Elimination–Addition
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.