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Treatment of meso 2-ethylhexyl-3-mercaptopropionate substituted porphyrins with base at room temperature generated a porphyrin thiolate anion which in situ reacted in a nucleophilic aromatic substitution (SNAr) reaction with remaining thioether derivative. This reaction yielded S-linked bisporphyrins in good yields, with mechanistic insight obtained via displacement reactions. Additionally, SNAr of the thioether chain was achieved using S- and organolithium nucleophiles.

From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual SNAr via thiolate displacement?

From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual S_NAr via thiolate displacement?