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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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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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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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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 para...
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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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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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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.
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Author Spotlight: Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers
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Metal-Free Aryl Cross-Coupling Directed by Traceless Linkers.

Veit G Haensch1, Toni Neuwirth1, Johannes Steinmetzer2

  • 1Department of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology, HKI, Beutenbergstrasse 11a, 07745, Jena, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 18, 2019
PubMed
Summary

A new metal-free photochemical method called photosplicing enables the selective synthesis of biaryls. This reaction proceeds via an excited state mechanism, offering a unique approach for creating diverse biaryl compounds without metals or radicals.

Keywords:
biarylscross-couplingdensity functional calculationsphotochemistrysynthetic methods

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Synthetic Methodology

Background:

  • The synthesis of biaryl compounds is crucial in organic chemistry.
  • Existing methods often rely on transition metals or harsh conditions, posing challenges for selectivity and sustainability.
  • Developing metal-free and highly selective synthetic routes remains a significant goal.

Purpose of the Study:

  • To report the scope and mechanism of a novel photochemical approach for synthesizing (hetero)biaryls.
  • To demonstrate the utility of photosplicing as a metal-free and radical-free cross-coupling method.
  • To elucidate the mechanistic pathway of the photosplicing reaction.

Main Methods:

  • Investigated the photochemical fusion of aryl substituents using a traceless sulfonamide linker (photosplicing).
  • Explored reaction conditions and tested diverse synthetic probes (40 examples, including heterocycles).
  • Employed quantum chemical calculations to understand the reaction mechanism.

Main Results:

  • Photosplicing exhibits a broad scope for synthesizing various (hetero)biaryls.
  • The reaction is metal-free and does not involve radical intermediates.
  • Quantum chemical calculations indicate an intramolecular photochemical process involving an excited singlet state and a five-membered transition state, leading to ipso-ipso coupling.

Conclusions:

  • Photosplicing is a unique and effective method for aryl cross-coupling in the excited state.
  • This approach provides a versatile route for the synthesis of a wide range of biaryl compounds.
  • The metal-free and selective nature of photosplicing offers advantages over traditional methods.