Journal
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
Volume 25, Issue 7-8, Pages 664-673Publisher
WORLD SCIENTIFIC PUBL CO PTE LTD
DOI: 10.1142/S1088424621500619
Keywords
dipyrromethane; porphyrin; arylglyoxylic acid; K2S2O8
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Funding
- CSIR, New Delhi [02(0337)/18/EMR-II]
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The study reports a method for synthesizing dipyrromethanes at 90°C in the presence of K(2)S(2)O(8) with high yields. The method avoids the use of excess pyrrole, using instead a stoichiometric amount, and demonstrates potential for scale-up production of dipyrromethanes.
The synthesis of dipyrromethanes from pyrrole and arylglyoxylic acids in the presence of K(2)S(2)O(8)at 90 circle C is reported affording dipyrromethanes in very good yields. Unlike an excess pyrrole traditionally used in dipyrromethane synthesis, the current method uses a stoichiometric amount of pyrrole avoiding any use of Bronsted or Lewis acid. A gram scale synthesis of 5-phenyldipyrromethane is also achieved demonstrating potential scale up of dipyrromethanes using this method feasible. Subsequently, dipyrromethanes were converted to A(4)-tetraarylporphyrins also in the presence of K(2)S(2)O(8)at 90 circle C. A direct synthesis of A(4)-tetraphenylporphyrin from excess pyrrole and phenylglyoxylic acid in the presence of K2S2O8 at 90 circle C is also reported.
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