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Related Concept Videos

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.2K
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.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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.
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic 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,...
2.1K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

3.8K
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...
3.8K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

15.8K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
15.8K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
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...
4.0K

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Updated: Jul 8, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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An efficient and chemoselective method to generate arynes.

Bryan E Metze1, Riley A Roberts1, Aleksandra Nilova1

  • 1Department of Chemistry, Portland State University Portland OR 97201 USA dstuart@pdx.edu.

Chemical Science
|December 11, 2023
PubMed
Summary
This summary is machine-generated.

This study introduces a mild and efficient method for generating arynes using aryl(TMP)iodonium salts and potassium phosphate. This approach demonstrates broad functional group compatibility, overcoming limitations of previous aryne generation techniques.

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Reactive Intermediates

Background:

  • Arynes are versatile reactive intermediates in organic synthesis.
  • Previous methods for aryne generation suffer from poor functional group compatibility, limiting their application.
  • Developing mild and efficient aryne generation protocols is crucial for expanding their synthetic utility.

Purpose of the Study:

  • To develop a new, mild, and efficient method for generating arynes.
  • To investigate the functional group compatibility of the developed aryne generation method.
  • To quantitatively compare the functional group tolerance of different aryne generation strategies.

Main Methods:

  • Aryne generation via deprotonation of arenes and elimination of "onium" leaving groups using aryl(TMP)iodonium salts (TMP = 2,4,6-trimethoxyphenyl).
  • Utilizing potassium phosphate as a mild base.
  • Compatibility studies with various arynophiles and sensitive functional groups (Lewis acids, Brønsted acids, electrophiles).
  • Quantitative analysis of functional group compatibility for different aryne generation methods.

Main Results:

  • A mild, efficient, and broad-scope method for aryne generation was established.
  • The developed method demonstrates compatibility with a wide range of arynophiles.
  • The study presents the first quantitative analysis comparing functional group compatibility across multiple aryne generation techniques.
  • Sensitive functional groups, including Lewis acids, Brønsted acids, and electrophiles, were found to be compatible with the new method.

Conclusions:

  • Aryl(TMP)iodonium salts provide a superior precursor for mild and efficient aryne generation.
  • The developed method significantly broadens the scope of aryne chemistry by accommodating sensitive functional groups.
  • This work overcomes key limitations in aryne synthesis, paving the way for wider adoption in organic synthesis.