One-Pot Synthesis of Four Chlorin Derivatives by a Divergent Ylide

The Journal of Organic Chemistry
Junior GonzalesCharles Michael Drain

Abstract

Chlorins have unique photophysical properties that are exploited in diverse biological and materials applications. De novo chlorin synthesis with specific exocyclic motifs can be challenging and many are not stable to photobleaching and/or oxidation. A facile approach to a stable synthetic chlorin with a fused N-methyl pyrrolidine uses cyclo addition of a sarcosine-based azomethine ylide on 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)-porphyrin (TPPF20) is reported, but this approach has limitations. We report the synthesis of stable chlorin scaffolds starting with TPPF20 using a new glycine-based N-(hydroxymethyl)- N-methelenemethanideaminium ylide. Careful control of the 1,3-dipolar cycloaddition reaction allows a divergent use of the glycine derived ylide to yield four new chlorins, including the fused NH-pyrrolidine, two dimers, and the same N-methyl chlorin product from the sarcosine ylide reaction. The mechanism begins with the formation of a bis(hydroxymethyl)glycine, which then dehydrates and decarboxylates to form the active N-(hydroxymethyl)- N-methelenemethanideaminium ylide, which then reacts with TPPF20 to form a key N-(hydroxymethyl)-17,18-pyrrolidinyl-chlorin intermediate. Deformylation of this intermediate a...Continue Reading

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Mar 18, 2017·Chemical Communications : Chem Comm·Junior GonzalesCharles Michael Drain

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Citations

Sep 19, 2020·Chemical Communications : Chem Comm·Javier Hernández-GilJunior Gonzales
Jan 7, 2021·Molecular Pharmaceutics·Junior GonzalesThomas Reiner
Aug 4, 2021·Photochemistry and Photobiology·Amit AggarwalSunaina Singh

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