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Strategies for Corrole Functionalization.

Joana F B Barata1, M Graça P M S Neves1, M Amparo F Faustino1

  • 1Department of Chemistry and QOPNA, and ‡Department of Chemistry and CICECO, University of Aveiro , 3810-193 Aveiro, Portugal.

Chemical Reviews
|February 23, 2017
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This review details the diverse functionalization reactions of meso-arylcorroles, covering both core and peripheral modifications. It explores synthesis, N-alkylation, and various reactions like substitution and cycloadditions for these important macrocycles.

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Area of Science:

  • Organic Chemistry
  • Macrocyclic Chemistry

Background:

  • Corroles are macrocyclic compounds with unique electronic and structural properties.
  • Functionalization of corroles is crucial for tuning their properties and expanding their applications.

Purpose of the Study:

  • To provide a comprehensive overview of the functionalization reactions of meso-arylcorroles.
  • To detail synthetic methods and reaction mechanisms for corrole modification.

Main Methods:

  • Review of experimental details for metallocorrole synthesis and N-alkylation.
  • Detailed discussion of peripheral functionalization reactions including halogenation, formylation, and nitration.
  • Analysis of corrole participation in nucleophilic aromatic substitution and cycloaddition reactions (Diels-Alder, 1,3-dipolar).

Main Results:

  • Encompasses a wide array of functionalization reactions: Wittig, reactions with active methylene compounds, amine/amide/imine formation, and metal-catalyzed reactions.
  • Describes oxidation and ring expansion reactions of the corrole macrocycle.
  • Highlights the versatility of corrole chemistry for creating complex molecular architectures.

Conclusions:

  • Meso-arylcorroles offer a versatile platform for diverse chemical modifications.
  • Understanding these functionalization reactions is key to advancing corrole chemistry and its applications.
  • This review serves as a valuable resource for researchers in the field of macrocyclic chemistry.