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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

12.5K
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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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.3K
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...
5.3K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.9K
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,...
2.9K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

18.6K
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.
18.6K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

5.1K
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...
5.1K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

21.7K
Introduction
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.
21.7K

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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Synthesis of biaryls using aryne intermediates.

José-Antonio García-López1, Michael F Greaney

  • 1Dpto. Química Inorgánica, Universidad de Murcia, Campus de Espinardo, Murcia, 30100, Spain. joangalo@um.es.

Chemical Society Reviews
|October 19, 2016
PubMed
Summary

Aryne chemistry provides a powerful alternative to metal-catalyzed cross-coupling for synthesizing biaryls. Modern methods using new precursors enable diverse biaryl structures under mild conditions.

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Biaryl synthesis is crucial in medicinal chemistry and materials science.
  • Traditional metal-catalyzed cross-coupling methods have limitations.
  • Benzyne intermediates offer an alternative synthetic strategy.

Purpose of the Study:

  • To review aryne methods for biaryl synthesis.
  • To highlight the evolution from early observations to modern techniques.
  • To showcase the versatility of benzyne chemistry.

Main Methods:

  • Review of historical and modern literature on benzyne chemistry.
  • Focus on halobenzene precursors, 2-(trimethylsilyl)phenyl triflates, and tri-ynes.
  • Analysis of reaction scope and conditions.

Main Results:

  • Benzyne chemistry has evolved significantly since 1940.
  • Diverse biaryl structures can be accessed via aryne intermediates.
  • Modern precursors allow for mild reaction conditions.

Conclusions:

  • Aryne chemistry is a powerful and versatile tool for biaryl synthesis.
  • It offers a valuable alternative to conventional cross-coupling methods.
  • Customizable substrates enable access to a wide range of biaryl structures.