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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.1K
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 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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

Nucleophilic Aromatic Substitution: Elimination–Addition

4.1K
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...
4.1K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.8K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.8K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
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,...
2.2K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

10.3K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Ruthenium-Catalyzed Cycloaddition of Azides and Selenoalkynes with Built-in "Catch-and-Release" Functionality.

Qiang Feng1, Yu Tan2, Liang Chen1

  • 1Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.

Angewandte Chemie (International Ed. in English)
|August 7, 2025
PubMed
Summary

Researchers developed a new click reaction using selenoalkynes for mild cross-linking and easy bond cleavage. This versatile "catch-and-release" method shows promise for various biomedical applications.

Keywords:
Bioorthogonal reactionsCleavage reactionsCycloadditionSelenium

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Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Chemical Biology

Background:

  • Click chemistry is essential for bioconjugation and drug discovery.
  • Reactions with "catch-and-release" capabilities, enabling both cross-linking and cleavage, are highly sought after but scarce.
  • Existing methods often lack efficiency, selectivity, or biocompatibility.

Purpose of the Study:

  • To introduce a novel click reaction based on selenoalkynes with "catch-and-release" functionality.
  • To demonstrate the utility of this reaction in chemical biology and biomedical contexts.
  • To provide a robust and versatile tool for chemists and biochemists.

Main Methods:

  • Development of a ruthenium-catalyzed click reaction between selenoalkynes and azides.
  • Investigation of reaction conditions, including catalyst loading, temperature, and reaction time.
  • Assessment of chemoselectivity, regioselectivity, and substrate scope.
  • Evaluation of functional group tolerance, solvent compatibility, and stability in air and water.
  • Demonstration of biocompatibility with biomolecules.

Main Results:

  • A highly efficient ruthenium-catalyzed click reaction of selenoalkynes with azides was established.
  • The reaction exhibits excellent chemoselectivity and regioselectivity under mild conditions.
  • The selenoalkyne adducts allow for facile cleavage of the carbon-selenium bond, enabling "catch-and-release" functionality.
  • The protocol demonstrates broad substrate scope and good tolerance of various functional groups, solvents, air, and water.
  • Compatibility with biomolecules was confirmed, highlighting its potential for biological applications.

Conclusions:

  • A novel and robust selenoalkyne-based click reaction with "catch-and-release" capabilities has been developed.
  • This reaction offers a valuable new tool for bioconjugation, chemical biology, and potential biomedical applications.
  • The demonstrated mild conditions, high efficiency, and biocompatibility make it an attractive alternative to existing methods.