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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
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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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Aryl Triflates in On-Surface Chemistry.

Jindong Ren1,2, Henning Klaasen3, Melanie C Witteler3,4

  • 1Center for Nanotechnology (CeNTech), Heisenbergstraße 11, 48149, Münster, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 31, 2020
PubMed
Summary

Aryl triflates undergo regioselective C-C coupling on copper surfaces. The triflate group facilitates coupling via radical intermediates, forming conjugated oligomers.

Keywords:
STMaryl triflatehomo couplingself-assemblysurface chemistry

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Area of Science:

  • Surface chemistry
  • Organic synthesis
  • Materials science

Background:

  • Aryl triflates are versatile synthetic intermediates.
  • On-surface synthesis offers unique pathways for material fabrication.
  • Controlling regioselectivity in C-C coupling is crucial for constructing complex molecules.

Purpose of the Study:

  • To investigate the reactivity of aryl triflates in on-surface C-C coupling reactions.
  • To elucidate the mechanism of triflate-directed homo coupling on metal surfaces.
  • To synthesize novel oligomeric conjugated π-systems using aryl triflates as monomers.

Main Methods:

  • On-surface synthesis on a Cu(111) surface.
  • Scanning tunneling microscopy (STM) for analyzing reactants, intermediates, and products.
  • Density Functional Theory (DFT) calculations to support proposed mechanisms and structures.

Main Results:

  • Aryl triflates undergo regioselective homo coupling on Cu(111) via hydrodetriflation.
  • A cascade mechanism involving aryloxy and aryl radicals was identified.
  • Oligomeric conjugated π-systems were successfully synthesized.
  • Steric hindrance influences the regioselectivity of the coupling reaction.

Conclusions:

  • The triflate group is an effective directing group for on-surface C-C coupling.
  • The study provides a detailed mechanistic understanding of the coupling process.
  • This method enables the construction of well-defined conjugated oligomers on surfaces.