Related Experiment Video
Updated: Dec 23, 2025
12:27
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
11.2K
An allenylidene Au(i) catalyst derived from triazole units and its initial application
Bai-Ling Chen1, Yuan Zhang1, Ya-Ru Lei1
1Department of Chemistry, Renmin University of China, 59# Zhongguanchun street, Haidian District, Beijing 100872, China. zilichen@ruc.edu.cn.
Chemical Communications (Cambridge, England)
|April 24, 2020
Summary
A novel allenylidene gold(I) catalyst was developed, showing enhanced catalytic activity in the gold-catalyzed Nazarov reaction. This new catalyst offers superior performance compared to existing gold complexes for aryl enone transformations.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Organic Synthesis
Background:
- Gold(I) complexes are effective catalysts for various organic transformations.
- Nazarov cyclization is a key reaction for forming cyclopentenones.
- Development of novel ligands can enhance catalyst performance.
Purpose of the Study:
- To synthesize and characterize a novel allenylidene gold(I) catalyst.
- To evaluate the catalytic activity of the new catalyst in the Nazarov reaction.
- To compare its performance against established gold catalysts.
Main Methods:
- Synthesis of triazolylidene-based allenylidene gold(I) complexes.
- Characterization using spectroscopic techniques.
- Application in the gold-catalyzed Nazarov reaction of aryl enones.
Main Results:
- The novel allenylidene Au(I) catalyst demonstrated high σ-donating and enhanced π-accepting ligand properties.
- Superior catalytic activities were observed in the Nazarov reaction compared to IPrAuCl, Ph3PAuCl, and (PhO)3PAuCl.
- Efficient cyclization of aryl enones was achieved.
Conclusions:
- A new class of allenylidene Au(I) catalysts has been successfully developed.
- These catalysts exhibit enhanced reactivity and efficiency in gold-catalyzed reactions.
- This work provides a promising new tool for organic synthesis, particularly for Nazarov cyclizations.
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
Related Concept Videos
01:22Preparation of 1° Amines: Azide Synthesis
4.5K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.5K
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
8.8K
Introduction
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.
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.
8.8K
02:27Preparation of Alkynes: Alkylation Reaction
11.8K
Introduction
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.
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.
11.8K
01:19Diazonium Group Substitution: –OH and –H
3.2K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.2K
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
3.8K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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...
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...
3.8K
01:28Preparation of 1° Amines: Gabriel Synthesis
4.3K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
4.3K