Efficient Synthesis of meso-Tetraarylporphyrins Using I₂ as Catalyst and IBX as Oxidant

Abstract

meso-Tetraarylporphyrins are synthesized from pyrrole and substituted benzaldehydes by a catalytic amount of I₂ as catalyst and o-iodoxybenzoic acid (IBX) as oxidant in two steps and one flask. The advantages of this method include the use of inexpensive and easily available catalyst, avoidance of heavy consumption of CH₂Cl₂, innocuous oxidant, and good yields.

Keywords:

• Aldehydes
• IBX
• meso-tetraarylporphyrins
• pyrrole
• synthesis

ACKNOWLEDGMENT

This work was supported by the National Program on Key Basic Research Projects of China (973 Program, 2005 CB724306).

Notes

^a Reactions were performed with 1 mmol pyrrole, 1 mmol benzaldehyde, and 0.025 mmol iodine at rt. After step 1 was completed, 1 mmol IBX was added to the solution and refluxed at 39°C.

^b Isolated yields.

^a Reactions were performed with 1 mmol pyrrole, 1 mmol benzaldehyde, and 0.025 mmol iodine in 15 ml CH₂Cl₂ at rt. After step 1 was completed, IBX was added.

^b The reaction temperature is room temperature.

^c Isolated yields.

^a Reactions were performed with 1 mmol benzaldehyde, 1 mmol pyrrole, and 0.025 mmol iodine in 15 ml CH₂Cl₂ at rt. After step 1 was completed, 1 mmol IBX was added to the solution and refluxed at 39°C.

^b Isolated yields.