Related Experiment Video
Updated: Apr 28, 2026
09:58
Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
12.3K
General method for functionalized polyaryl synthesis via aryne intermediates
Thanh Truong1, Milad Mesgar, Ky Khac Anh Le
1Department of Chemistry, University of Houston , Houston, Texas 77204-5003, United States.
Journal of the American Chemical Society
|June 4, 2014
Summary
This study introduces a novel base-promoted arylation method for arenes and heterocycles. This technique offers a new route to complex polyaromatic compounds, complementing existing methods.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
Background:
- Direct arylation methods are crucial for synthesizing polyaromatic compounds.
- Existing transition-metal-catalyzed methods have limitations in substrate scope and accessibility.
Purpose of the Study:
- To develop a new base-promoted arylation strategy.
- To enable the synthesis of highly functionalized polyaryls.
- To complement existing direct arylation techniques.
Main Methods:
- Base-promoted arylation of arenes and heterocycles using aryl halides and triflates.
- In situ electrophilic trapping of aryllithium (ArLi) intermediates generated from benzyne reactions.
Main Results:
- Successful arylation of arenes and heterocycles.
- Rapid and facile synthesis of diverse, highly functionalized polyaryls.
- Demonstrated tolerance of various functional groups including alkenes, ethers, and halides.
Conclusions:
- The developed base-promoted arylation methodology provides an alternative to transition-metal catalysis.
- This method expands access to complex polyaromatic structures not easily synthesized otherwise.
- High functional group tolerance ensures broad applicability in organic synthesis.
More Related Videos
Related Concept Videos
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
2.1K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.1K
02:27Preparation of Alkynes: Alkylation Reaction
9.3K
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.
9.3K
01:11Nucleophilic Aromatic Substitution: Elimination–Addition
2.9K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
2.9K
01:22Preparation of 1° Amines: Azide Synthesis
2.6K
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...
2.6K
01:30Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
3.0K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
3.0K
01:11Aryldiazonium Salts to Azo Dyes: Diazo Coupling
3.2K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
3.2K