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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Preparation of Alkynes: Alkylation Reaction02:27

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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 of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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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,...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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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...
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Preparation of Alkynes: Dehydrohalogenation02:34

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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.
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Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

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Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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One-pot, three-component arylalkynyl sulfone synthesis.

C Chun Chen1, Jerome Waser

  • 1Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne , EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland.

Organic Letters
|January 31, 2015
PubMed
Summary
This summary is machine-generated.

A new one-pot method efficiently synthesizes arylsulfonyl alkynes using ethynyl-benziodoxolone reagents and DABSO. This approach yields a diverse array of valuable aryl and heteroarylalkynyl sulfones.

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Area of Science:

  • Organic Synthesis
  • Organometallic Chemistry
  • Sulfur Chemistry

Background:

  • Arylsulfonyl alkynes are important synthetic intermediates.
  • Existing methods for their preparation can be limited in scope or efficiency.

Purpose of the Study:

  • To develop a novel, efficient, and versatile one-pot protocol for synthesizing arylsulfonyl alkynes.
  • To explore the utility of ethynyl-benziodoxolone (EBX) reagents and DABSO in a three-component reaction.

Main Methods:

  • A one-pot, three-component reaction involving ethynyl-benziodoxolone (EBX) reagents, DABSO (DABCO·SO2), and either organomagnesium reagents or aryl iodides.
  • Palladium catalysis was employed to facilitate the coupling.

Main Results:

  • Successfully prepared a broad range of aryl and heteroarylalkynyl sulfones.
  • Achieved overall yields ranging from 46-85% for the target compounds.

Conclusions:

  • The reported protocol offers a convenient and effective route to arylsulfonyl alkynes.
  • This method expands the synthetic toolbox for accessing valuable sulfur-containing alkynes.