From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual S sub(N)Ar viathiolate displacement?

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From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual S sub(N)Ar viathiolate displacement?

Ryan, Aoife A; Plunkett, Shane; Casey, Aoife; McCabe, Thomas; Senge, Mathias O

Chemical communications (Cambridge, England), 12/2013, Volume: 50, Issue: 3

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Treatment of meso2-ethylhexyl-3-mercaptopropionate substituted porphyrins with base at room temperature generated a porphyrin thiolate anion which in situreacted in a nucleophilic aromatic substitution (S sub(N)Ar) reaction with remaining thioether derivative. This reaction yielded S-linked bisporphyrins in good yields, with mechanistic insight obtained viadisplacement reactions. Additionally, S sub(N)Ar of the thioether chain was achieved using S- and organolithium nucleophiles.

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Ryan, Aoife A | Plunkett, Shane | Casey, Aoife | McCabe, Thomas | Senge, Mathias O

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