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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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"Golden" Cascade Cyclization to Benzo[c]-Phenanthridines.

Christoph M Hendrich1, Sebastian Senn1, Lea Haas1

  • 1Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 26, 2021
PubMed
Summary

This study introduces a gold-catalyzed domino reaction for synthesizing novel dihydrobenzo[c]phenanthridines. The developed method efficiently produces π-extended molecules, showing promise for organic semiconductor applications.

Keywords:
benzo[c]phenanthridinesbenzylaminescascade reactionshomogeneous gold catalysis

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Materials Science

Background:

  • Dihydrobenzo[c]phenanthridines are important heterocyclic compounds.
  • Efficient synthesis of π-extended derivatives is crucial for advanced materials.

Purpose of the Study:

  • To develop a novel gold-catalyzed cascade cyclization for dihydrobenzo[c]phenanthridines.
  • To explore the scope and applications of the synthesized compounds.

Main Methods:

  • Gold-catalyzed domino reaction involving Boc-protected benzylamines with two tethered alkyne moieties.
  • Initiation via 6-endo-dig cyclization.
  • Optimization through extensive screening and exploration of reaction scope.

Main Results:

  • Synthesis of nine new Boc-protected dihydrobenzo[c]phenanthridines with yields up to 98%.
  • Successful π-extension and bidirectional approaches.
  • Quantitative yields of substituted benzo[c]phenanthridines after Boc deprotection and oxidation.
  • Demonstrated utility of π-extended molecules as organic semiconductors in thin-film transistors.

Conclusions:

  • A novel and efficient gold-catalyzed cascade cyclization has been established.
  • The synthesized π-extended dihydrobenzo[c]phenanthridines exhibit potential as organic semiconductors.