Issue 21, 2024

A divergent one-pot thiol-Michael strategy to create β-thiophene-fused porphyrins

Abstract

A divergent one-pot domino strategy for the synthesis of nickel(II) and copper(II) β-thiophene-fused 5,10,15,20-tetraarylporphyrins was developed through a thiol-Michael addition of thioglycolic/thiolactic acid to the corresponding 2-iminoporphyrins, formed in situ after the reaction of nickel(II) and copper(II) 2-formyl-5,10,15,20-tetraarylporphyrins with sterically hindered tert-butylamine in 1,2-dichloroethane at 80 °C. Interestingly, the reaction of 2-formylporphyrins with comparatively less sterically hindered primary amines and thioglycolic acid afforded a mixture of β-substituted porphyrinic thiazolidinones and β-thiophene-fused porphyrins. A similar one-pot thiol-Michael protocol was applied to construct a novel free-base thieno[2,3-b]-meso-tetrakis(4-methoxyphenyl)porphyrin, which underwent zinc insertion by using zinc acetate in a CHCl3–MeOH mixture and afforded zinc(II) β-thiophene-fused meso-tetrakis(4-methoxyphenyl)porphyrin in an appreciable isolated yield. On photophysical evaluation, these new porphyrins displayed a modest bathochromically shifted electronic absorption in contrast to meso-tetraarylporphyrin building blocks.

Graphical abstract: A divergent one-pot thiol-Michael strategy to create β-thiophene-fused porphyrins

Supplementary files

Article information

Article type
Paper
Submitted
11 Apr 2024
Accepted
08 May 2024
First published
08 May 2024

Org. Biomol. Chem., 2024,22, 4369-4377

A divergent one-pot thiol-Michael strategy to create β-thiophene-fused porphyrins

J. Singh, A. Singh and M. Nath, Org. Biomol. Chem., 2024, 22, 4369 DOI: 10.1039/D4OB00598H

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