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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

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9,10,19,20-Tetraarylporphycenes.

K S Anju¹, S Ramakrishnan, Ajesh P Thomas

¹Photosciences and Photonics Section, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (NIIST-CSIR), Trivandrum-695019, Kerala, India.

Organic Letters

|December 5, 2008

Summary

Synthesized meso-tetraarylporphycenes, structural isomers of tetraarylporphyrins, using a novel acid-catalyzed oxidative coupling. This new method offers an alternative to traditional McMurry coupling for creating these unique macrocycles.

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Area of Science:

Organic Chemistry
Supramolecular Chemistry
Materials Science

Background:

Meso-tetraarylporphycenes are structural isomers of meso-tetraarylporphyrins.
Traditional synthesis of such macrocycles often relies on McMurry coupling reactions.

Purpose of the Study:

To develop a new synthetic methodology for meso-tetraarylporphycenes.
To explore an alternative to the McMurry coupling reaction for synthesizing these compounds.

Main Methods:

Acid-catalyzed oxidative coupling reaction for the synthesis of meso-tetraarylporphycenes.
Single-crystal X-ray diffraction analysis for structural characterization of the macrocycle and its Ni(II) complex.

Main Results:

Successful synthesis of meso-tetraarylporphycenes via acid-catalyzed oxidative coupling.
Structural elucidation revealing the formation of 1-D supramolecular assembly in both the macrocycle and its Ni(II) complex.

Conclusions:

The acid-catalyzed oxidative coupling reaction is a viable and novel method for synthesizing meso-tetraarylporphycenes.
The characterized macrocycles and their Ni(II) complexes exhibit self-assembly into 1-D supramolecular structures.